Substituted pyrimidine and pyridine herbicides

ABSTRACT

Compounds of formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein J is (J-1), (J-2), (J-3), (J-4), (J-5), (J-6) or (J-7); and J, W, X, Y, Z, A, R 1 -R 8  are as defined in the disclosure. Also disclosed are compositions containing the compounds of formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of formula (I).

CROSS REFERENCE TO RELATED APPLICATIONS

This application was filed under 35 U.S.C. 371 from InternationalApplication PCT/US98/22088 filed Oct. 20, 1998 which claims prioritybenefit from Provisional Application No. 60/067,418 filed Dec. 3, 1997and Provisional Application No. 60/068,432 filed Dec. 22, 1997.

BACKGROUND OF THE INVENTION

This invention relates to certain pyrimidines and pyridines, theirN-oxides, agriculturally suitable salts, compositions thereof, andmethods of their use for controlling undesirable vegetation.

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet, corn(maize), potato, wheat, barley, tomato and plantation crops, amongothers, is very desirable. Unchecked weed growth in such useful cropscan cause significant reduction in productivity and thereby result inincreased costs to the consumer. The control of undesired vegetation innoncrop areas is also important. Many products are commerciallyavailable for these purposes, but the need continues for new compoundswhich are more effective, less costly, less toxic, environmentally saferor have different modes of action.

EP 723,960 discloses herbicidal substituted pyrimidines and pyridines ofFormula i:

wherein, inter alia,

A is an optionally substituted aryl or 5- or 6-membered nitrogencontaining heteroaromatic group;

X is oxygen or sulfur;

Z is nitrogen or CH;

R¹ and R² are independently hydrogen, halogen, alkyl, haloalkyl, nitroor cyano;

n is 0, 1 or 2; and

m is 0 to 5.

The pyrimidines and pyridines of the present invention are not disclosedin this reference.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including allgeometric and stereoisomers, N-oxides, and agriculturally suitable saltsthereof, as well as agricultural compositions containing them and amethod of their use for controlling undesirable vegetation:

W is N or CR¹¹;

X, Y and Z are independently N or CR¹²;

R¹ and R² are independently H, halogen, cyano, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₂-C₄ alkoxyalkyl, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkoxyalkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₄ alkenyloxy, C₃-C₄alkynyloxy, S(O)_(n)R¹³, C₂-C₄ alkylthioalkyl, C₂-C₄ alkylsulfonylalkyl,C₁-C₄ alkylamino or C₂-C₄ dialkylamino;

R³ is H, F, Cl, Br, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl or CO₂R¹⁴;

R⁴ is H, F, C₁-C₄ alkyl, OH or OR¹⁴;

R³ and R⁴ can be taken together with the carbon to which they areattached to form C(═O) or C(═NOR¹⁴);

R⁵ is halogen, cyano, SF₅, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-₄ haloalkoxy or S(O)_(n)R¹³;

R⁶ and R¹⁰ are independently H, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or S(O)_(n)R¹³;

R⁷ is halogen, cyano, SF₅, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy or S(O)_(n)R¹³;

R⁸ is C₁-C₄ alkyl or C₁-C₄ haloalkyl;

R⁹ is H, halogen, cyano, SF₅, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₄ alkenyloxy,C₃-C₄ alkynyloxy or S(O)_(n)R¹³;

R¹¹ is H, halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy or S(O)_(n)R¹³;

R¹² is H, halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy or S(O)_(n)R¹³;

each R¹³ is independently C₁-C₄ alkyl or C₁-C₄ haloalkyl;

each R¹⁴ is independently C₁-C₄ alkyl; and

each n is independently 0, 1 or 2.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2alkyl” indicates that one or two of the available positions for thatsubstituent may be alkyl which are independently selected. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy”includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy andthe different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl”denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” includeCH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.“Alkenyloxy” includes straight-chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkylthio”includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthiosubstitution on alkyl. Examples of “alkylthioalkyl” include CH₃SCH₂,CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group.Examples of “alkylsulfinyl” include CH₃S(O), CH₃CH₂S(O), CH₃CH₂CH₂S(O),(CH₃)₂CHS(O) and the different butylsulfinyl, pentylsulfinyl andhexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂,CH₃CH₂S(O)₂, CH₃CH₂CH₂S(O)₂, (CH₃)₂CHS(O)₂ and the differentbutylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Alkylamino”,“dialkylamino”, “alkenylthio”, “alkenylsulfinyl”, “alkenylsulfonyl”,“alkynylthio”, “allynylsulfinyl”, “alkynylsulfonyl”, and the like, aredefined analogously to the above examples. One skilled in the art willappreciate that not all nitrogen containing heterocycles can formN-oxides since the nitrogen requires an available lone pair foroxidation to the oxide; one skilled in the art will recognize thosenitrogen containing heterocycles which can form N-oxides. One skilled inthe art will also recognize that tertiary amines can form N-oxides.Synthetic methods for the preparation of N-oxides of heterocycles andtertiary amines are very well known by one skilled in the art includingthe oxidation of heterocycles and tertiary amines with peroxy acids suchas peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide,alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate,and dioxiranes such as dimethyldioxirane. These methods for thepreparation of N-oxides have been extensively described and reviewed inthe literature, see for example: T. L. Gilchrist in ComprehensiveOrganic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press;M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol.3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R.Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol.43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B.Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A.R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H.Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry,vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., AcademicPress.

The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. The term“1-2 halogen” indicates that one or two of the available positions forthat substituent may be halogen which are independently selected.Further, when used in compound words such as “haloalkyl”, said alkyl maybe partially or fully substituted with halogen atoms which may be thesame or different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂and CF₃CCl₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O,HCF₂CH₂CH₂O and CF₃CH₂O.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 4. Forexample, C₁-C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. Examples of “alkylcarbonyl”include C(O)CH₃, C(O)CH₂CH₂CH₃ and C(O)CH(CH₃)₂. Examples of“alkoxycarbonyl” include CH₃OC(═O), CH₃CH₂OC(═O), CH₃CH₂CH₂OC(═O),(CH₃)₂CHOC(═O) and the different butoxy- or pentoxycarbonyl isomers. Inthe above recitations, when a compound of Formula I is comprised of oneor more heterocyclic rings, all substituents are attached to these ringsthrough any available carbon or nitrogen by replacement of a hydrogen onsaid carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for exampleR⁹, then, when this substituent is taken as hydrogen, it is recognizedthat this is equivalent to said group being unsubstituted.

The compounds of this invention thus include compounds of Formula I,geometric and stereoisomers thereof, N-oxides thereof, andagriculturally suitable salts thereof. The compound of this inventioncan exist as one or more stereoisomers. The various stereoisomersinclude enantiomers, diastereomers, atropisomers and geometric isomers.One skilled in the art will appreciate that one stereoisomer may be moreactive and/or may exhibit beneficial effects when enriched relative tothe other stereoisomer(s) or when separated from the otherstereoisomer(s). Additionally, the skilled artisan knows how toseparate, enrich, and/or to selectively prepare said stereoisomers. Thecompounds of the invention may be present as a mixture of stereoisomers,individual stereoisomers, or as an optically active form.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids.

Preferred compounds of the invention for reasons of better activityand/or ease of synthesis are:

Preferred 1. Compounds of Formula I above, geometric or stereoisomersthereof, N-oxides thereof and agriculturally-suitable salts thereof,wherein

R¹ and R² are independently H, C₁-C₄ alkyl or C₁-C₄ alkoxy;

R⁵ and R⁷ are independently halogen, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxyor S(O)_(n)R¹³;

R⁶ is H or F;

R⁸ is C₁-C₄ alkyl;

R⁹ is halogen, cyano, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkyl, C₁-C₄haloalkyl or S(O)_(n)R¹³;

R¹⁰ is H, halogen, cyano or C₁-C₄ haloalkyl;

R¹¹ is H, halogen, cyano or C₁-C₄ haloalkyl;

R¹² is H, halogen, cyano or C₁-C₄ haloalkyl; and

n is 0.

Preferred 2. Compounds of Preferred 1 wherein

W is N;

R⁵ and R⁷ are independently C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy; and

R⁹ is halogen, C₁-C₄ haloalkoxy, C₁-C₄ haloalkyl or S(O)_(n)R¹³.

Preferred 3. Compounds of Preferred 2 wherein

R¹ is C₁-C₄ alkyl or C₁-C₄ alkoxy;

R² is H;

R³ and R⁴ are independently H, F or methyl;

R⁵ and R⁷ are independently C₁-C₂ haloalkyl or C₁-C₂ haloalkoxy; and

R⁹ is C₁-C₂ haloalkoxy, C₁-C₂ haloalkyl or S(O)_(n)R¹³.

Preferred 4. Compounds of Preferred 3 wherein

J is J-1, J-5 or J-7.

Preferred 5. Compounds of Preferred 2 wherein

R³ and R⁴ can be taken together with the carbon to which they areattached to form C(═O).

Preferred 6. Compounds of Preferred 5 wherein

R¹ is C₁-C₄ alkyl or C₁-C₄ alkoxy;

R² is H;

R⁵ and R⁷ are independently C₁-C₂ haloalkyl or C₁-C₂ haloalkoxy; and

R⁹ is C₁-C₂ haloalkoxy, C₁-C₂ haloalkyl or S(O)_(n)R¹³.

Preferred 7. Compounds of Preferred 5 wherein

J is J-1 or J-5.

Most preferred is the compound of Formula I selected from the groupconsisting of:

(a)5-ethyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(b)5-ethyl-4-[[3-(trifluoromethyl)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(c)5-methyl-2-[4-(trifluoromethyl)phenyl]-4-[[3-(trifluoromethyl)phenyl]methyl]pyrimidine;

(d)5-methyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]pyrimidine;

(e)5-methyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(f)[5-methyl-2-[4-(trifluoromethyl)phenyl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone;

(g)[5-methyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone;and

(h)5-methyl-4-[[3-(trifluoromethyl)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine.

This invention also relates to herbicidal compositions comprisingherbicidally effective amounts of the compounds of the invention and atleast one of a surfactant, a solid diluent or a liquid diluent. Thepreferred compositions of the present invention are those which comprisethe above preferred compounds.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). The preferred methods of use arethose involving the above preferred compounds.

DETAILS OF THE INVENTION

The compounds of Formula I can be prepared by one or more of thefollowing methods and variations as described in Schemes 1-12. Thedefinitions of J, A, W, X, Y, Z, R¹, R², R³, R⁴, R⁹, R¹⁰, and R¹⁴ in thecompounds of Formulae 1-16 below are as defined above in the Summary ofthe Invention. Compounds of Formulae Ia-Ic are various subsets of thecompounds of Formula I, and all substituents for Formulae Ia-Ic are asdefined above for Formula I.

Scheme 1 illustrates the preparation of compounds of Formula Ia (FormulaI wherein A is A-1). Substituted heterocycles of Formula 1 (where L¹ ishalogen) can be coupled with metalated aryls or heteroaryls of Formula 2(where Met is Sn(alkyl)₃, B(OH)₂ or Zn(L¹)₂) in the presence of apalladium(O) catalyst such as tetrakis(triphenylphosphine)palladium(O)or in the presence of a palladium(II) catalyst such asdichlorobis(triphenylphosphine)palladium(II) to provide compounds ofFormula Ia. Palladium(II) catalysts are generally used with a suitablebase such as aqueous sodium bicarbonate or sodium carbonate. Suitablesolvents for this coupling include N,N-dimethylformamide,dimethoxyethane, acetonitrile or tetrahydrofuran. Reaction temperaturesrange from 20° C. to 130° C.

Scheme 2 illustrates the preparation of compounds of Formula Ib (FormulaI wherein A is A-2). Substituted heterocycles of Formula 1 are allowedto react with substituted azoles of Formula 3 in the presence of asuitable base such as an alkali carbonate, alkali hydroxide, or alkalihydride in a solvent such as N,N-dimethylfornamide, acetonitrile ortetrahydrofuran at temperatures ranging from 0° C. to 130° C. to providecompounds of Formula Ib.

Scheme 3 illustrates a method for preparing compounds of Formula Icwherein J is an azole heterocycle of Formula J-7 and A is A-1 or A-2.Compounds of Formula 4 are allowed to react with an azole heterocycle ofFormula 3 in a protic or aprotic solvent at temperatures ranging from 0°C. to 100° C. in the presence of a suitable base such an alkalicarbonate, alkali hydroxide, or alkali hydride to provide compounds ofFormula Ic. Particularly suitable are potassium carbonate as base andacetonitrile or N,N-dimethylformamide as solvent at a reactiontemperature range of 20° C. to 80° C.

Substituted pyrimidine intermediates of Formula 1 (wherein J is J-1 toJ-6) can be prepared by the method shown in Scheme 4. By the syntheticprotocol of Menta, E. and Oliva, A. J. Heterocyclic Chem. (1997), 34, p27, a dihalopyrimidine of Formula 5 (where L¹ and L² are halogen) iscoupled with a substituted alkyl zinc reagent of Formula 6 (where L³ ishalogen) in the presence of a palladium(O) catalyst such astetrakis(triphenylphosphine)palladium(O) or in the presence of apalladium(II) catalyst such asdichloro-bis(triphenylphosphine)palladium(II). Palladium(II) catalystsare generally used with a suitable base such as sodium bicarbonate orsodium carbonate. Suitable solvents for this coupling includeN,N-dimethylformamide, dimethoxyethane, acetonitrile or tetrahydrofuran.Reaction temperatures range from 0° C. to 130° C.

Metalated aryls and heteroaryls of Formula 2 can be obtainedcommercially or can be prepared by methods known in the art: Sandosham,J. and Undheim, K. Tetrahedron (1994), 50, pp 275-284; Undheim, K. andBenneche, T. Acta Chemica Scandinavica (1993), 47, pp 102-121; Advancesin Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: NewYork, 1995; volume 62, pp 305-418.

Azoles of Formula 3 can be obtained commercially or can be prepared bymethods known in the art Elguero, J. et al., Organic Preparations andProcedures Int. (1995), 27, pp 33-74; Comprehensive HeterocyclicChemistry; Potts, K., Ed.; Pergamon Press: New York, 1984; volume 5,chapters 4.04-4.13; Heterocyclic Compounds; Elderfield, R., Ed.; JohnWiley: New York, 1957; volume 5, chapters 2 and 4; Baldwin, J. et al. J.Med. Chem., (1975), 18, pp 895-900; Evans, J. J. et al. U.S. Pat. No.4,038,405.

Dihaloheterocycles of Formula 5 can be obtained commercially or can bereadily prepared by known methods in the art; for example, see Advancesin Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: NewYork, 1993; volume 58, pp 301-305; Heterocyclic Compounds; Elderfield,R. C., Ed.; John Wiley: New York, 1957; volume 6, chapter 7, pp 265-270.

Zinc reagents of Formula 6 can be made by the method shown in Scheme 5.A substituted alkyl halide of Formula 7 (where L³ is halogen) is allowedto react with activated zinc (see Jubert, C. and Knochel, P. J. Org.Chem. (1992), 57, p 5425; Knochel, P. and Singer, R. D. Chem. Rev.(1993), 93, p 2117) in a suitable solvent such as N,N-dimethylformamide,dimethoxyethane, acetonitrile or tetrahydrofuran. Reaction temperaturesrange from 0° C. to 130° C.

As shown in Scheme 6, heterocyclic benzylic bromides of Formula 4 can bemade by bromination of heterocycles of Formula 8 with bromine in anacidic solvent such as acetic acid at temperatures ranging from 20° C.to 100° C. (see, for example, Strekowski et al. J. Org. Chem. (1992),56, p 5610).

Heterocycles of Formula 8 can be made from precursor heterocycles ofFormula 9 as shown in Scheme 7. The addition of lithium or Grignardreagents of formula R³R⁴CHLi or R³R⁴CHMgL¹ to heterocycles of Formula 9is carried out in ethereal solvents such as ether or tetrahydrofuran attemperatures ranging from −70° C. to 30° C. The reaction mixture isworked up by the addition of water and an oxidizing agent. Aparticularly suitable oxidizing agent is dichlorodicyanoquinone (DDQ).See Strekowski et al. J. Org. Chem. (1992), 56, p 5610 for examples ofthis synthetic method.

Heterocycles of Formula 9 can be prepared according to methods taught byStrekowski et al. J. Org. Chem. (1992), 56, p 5610; Bredereck et. al.,Chem. Ber. (1960), 93, p 1208; Burdeska et al. Helv. Chim. Acta (1981),64, p 113; Undheim, K. and Benneche, T. Advances in HeterocyclicChemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1995, volume62, pp 305-418; and Comprehensive Heterocyclic Chemistry; Boulton, A.J., and McKillop, A., Eds.; Pergamon Press: New York, 1984; volume 3,chapter 2.13. Lithium and Grignard reagents of formulae R³R⁴CHLi orR³R⁴CHMgL¹ are commercially available or can be prepared by methods wellknown in the art.

Compounds of Formula 1 (wherein R³ and R⁴ are taken together as C(═O))can be prepared by the condensation of pyrimidines and pyridines ofFormula 10 with aldehydes of Formula 11 in the presence of animidazolium catalyst of Formula 12 as shown in Scheme 8. This reactionis carried out in the presence of a strong base such as an alkalihydride, preferably sodium hydride, in solvents such as dichloromethane,dioxane, tetrahydrofuran, benzene, toluene or other aprotic solvent. Thereaction may be carried out at temperatures between 0 and 120° C. A widevariety of azolium salts are known to catalyze this transformation; see,for example, Miyashita Heterocycles, (1996), 43, 509-512 and referencescited therein. A preferred catalyst is 1,3-dimethylimidazolium iodide.

Compounds of Formula I (wherein R³ and R⁴ are taken together asC(═NOR¹⁴)) can be formed directly from compounds of Formula I (whereinR³ and R⁴ are taken together as C(═O)) by the action of hydroxylamine orcapped hydroxylamine salts of Formula 13 as shown in Scheme 9. Manyhydroxylamines are commercially available as acid salts and are freed bythe action of a base in the presence of the ketone of Formula I.Suitable bases include alkali carbonates, acetates, and hydroxides.These reactions are best carried out in protic solvents, such as loweralcohols, at temperatures between 0 and 120° C. Especially preferredconditions use sodium carbonate or sodium acetate as base in ethanol at70 to 80° C.

Compounds of Formula I (wherein R³ is OH and R⁴ is H) can be made by thereduction of ketones of Formula I (wherein R³ and R⁴ are taken togetheras C(═O)) as shown in Scheme 10. A wide variety of reduction conditionscan be utilized, but for reasons of ease of use and selectivity, alkaliborohydrides are preferred reductants. The reduction can be carried outat 0 to 100° C. in a variety of solvents which are inert to the actionof borohydrides. Especially preferred conditions are the use of sodiumborohydride in ethanol at 0 to 25° C.

As shown in Scheme 11, compounds of Formula 1 wherein J is J-7 can alsobe made via the bromination of compounds of Formula 14 with molecularbromine in an acidic solvent such as acetic acid at temperatures rangingfrom 20 to 100° C. in the same way as previously described in Scheme 6.The brominated products of Formula 15 can be displaced by heterocyclesof Formula 3 in the presence of a base such as potassium carbonate aspreviously described for Scheme 2. Compounds of Formula 14 are known inthe literature or are commercially available. See Benneche (Acta ChemicaScandanavia, 1997, 51, 302) for preparation of these compounds fromcompounds of Formula 5.

Compounds of Formula 1 in which R³ is cyano can be made as shown inScheme 12. The reaction of acetonitrile derivatives of formula 16 withcompounds of Formula 5 in the presence of a base gives compounds offormula 1 with a cyano group. The reaction can be carried out in avariety of solvents such as dimethylformamide, tetrahydrofuran, or othersolvents inert to strong bases. A wide variety of bases which candeprotonate substituted acetonitriles can be used. Sodium hydride andpotassium t-butoxide are preferred due to their ease of use andavailability. The reaction can be carried out at temperatures rangingfrom 0 to 100° C. Compounds of formula 16 are well known in theliterature and many are commercially available

Compounds of Formula I substituted with the group S(O)_(n)R¹³ wherein nis 1 or 2 can be prepared from compounds of Formula I substituted withsaid S(O)_(n)R¹³ group wherein n is 0 by treatment with an oxidizingreagent such as m-chloroperoxybenzoic acid or Oxone® (potassiumperoxymonosulfate). This type of oxidation reaction is well known in theart; for example, see March, J. Advanced Organic Chemistry; John Wiley:New York, 1992; 4^(th) edition, pp 1201-1203.

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula I may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula I. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula I.

One skilled in the art will also recognize that compounds of Formula Iand the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; s=singlet, d=doublet, t=triplet, q=quartet,m=multiplet, dd=doublet of doublets, dt=doublet of triplets, br s=broadsinglet.

EXAMPLE 1 Step A: Preparation of2-chloro-5-methyl-4-[[3-(trifluoromethyl)phenyl]methyl]pyrimidine

To a suspension of zinc dust (2.5 g, 38 mmol) stirred in 25 mL oftetrahydrofuran were added 2 drops of 1,2-dibromoethane and the mixturewas heated to reflux. The suspension was then cooled and 2 drops oftrimethylsilyl chloride were added followed by portionwise addition of3-(trifluoromethyl)benzyl bromide (6.0 g, 25 mmol) with heating. Whenthe reaction temperature reached 55° C., a strong exotherm occurred andthe reaction mixture was allowed to heat at reflux. The cooled reactionsolution was decanted into a solution of 2,4dichloro-5-methylpyrimidine(3.3 g, 20 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.44g, 0.63 mmol) stirring in 15 mL of tetrahydrofuran. Upon heating, thereaction mixture exothermed strongly again at 55° C. and was then heatedto reflux. The reaction mixture was allowed to cool and partitionedbetween diethyl ether and water. The organic layer was separated, washedwith 1 N aqueous hydrochloric acid and brine, dried over magnesiumchloride and concentrated under reduced pressure to give a crude oil.Purification by flash chromatography on silica gel (15 to 25% ethylacetate in hexane) yielded 2.4 g of the title compound of Step A as anoil. ¹H NMR (CDCl₃): δ8.35 (s, 1H), 7.60-7.35 (m, 4H), 4.15 (s, 2H),2.25 (s, 3H).

Step B: Preparation of5-methyl-2-[4-(trifluoromethyl)phenyl]-4-[[3-(trifluoromethyl)phenyl]methyl]pyrimidine

A stirred mixture of 4-(trifluoromethyl)benzene boronic acid (430 mg,2.3 mmol), the title compound of Step A (500 mg, 1.7 mmol),dichlorobis(triphenylphosphine)palladium(II) (120 mg, 0.17 mmol) andsodium carbonate (550 mg, 5.2 mmol) in a mixture of 6 mL of water and 2mL of tetrahydrofuran was heated at reflux for 1.5 h. The reactionmixture was then partitioned between diethyl ether and water. Theorganic layer was separated, washed with brine, dried over magnesiumsulfate and concentrated under reduced pressure. Flash chromatography onsilica gel (20 to 25% ethyl acetate in hexane) followed by triturationwith 10% diethyl ether in hexane afforded 350 mg of the title compoundof Step B, a compound of this invention, as a yellow-tinted solidmelting at 112-113° C. ¹H NMR (CDCl₃): δ8.55 (m, 3H), 7.70 (d, 2H), 7.60(s, 1H), 7.55-7.40 (m, 3H), 4.25 (s, 2H), 2.30 (s, 3H).

EXAMPLE 2 Step A: Preparation of5-methyl-4-[[3-(trifluoromethyl)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine

A stirred mixture of 3-(trifluoromethyl)pyrazole (390 mg, 2.9 mmol), thetitle compound of Step A in Example 1 (750 mg, 2.6 mmol), and powderedpotassium carbonate (1.1 g, 7.9 mmol) in 10 mL of N,N-dimethylformamidewas heated at 60° C. for 3 h followed by heating at 80° C. for 1 h. Thereaction mixture was then partitioned between diethyl ether and water.The organic layer was separated, washed with brine, dried over magnesiumsulfate and concentrated under reduced pressure. Column chromatographyon silica gel (5% diethyl ether in 1-chlorobutane) afforded 210 mg ofthe title compound of Step A as an oil which solidified to a white solidmelting at 90-92° C. ¹H NMR (CDCl₃): δ8.55 (t,2H), 7.55-7.50 (m, 2H),7.45-7.40 (m, 2H), 6.72 (d, 1H), 4.26 (s, 2H), 2.32 (s, 3H).

EXAMPLE 3 Step A: Preparation of5-methyl-2-(4-trifluoromethylphenyl)pyrimidine

A sample of 4-trifluoromethylbenzamidine hydrochloride dihydrate(Maybridge, 15.2 g, 58 mmol) was dissolved in 100 mL of methanol and3-ethoxy-2-methylacrolein (Janssen, 7.8 g, 64 mmol) was added. Sodiummethoxide (25% solution in methanol, 14.7 mL) was added and the mixturewas heated at 50° C. for 3 h. The cooled reaction mixture was then ddedto 500 ml of ice water and stirred for 30 minutes. The white solid wasfiltered, air dried, dissolved in 300 mL of dichloromethane and driedover magnesium sulfate. The solvent was removed under reduced pressureto yield, after trituration with hexanes, 12.5 g of the product as awhite solid melting at 143-146° C. ¹H NMR (CDCl₃): δ2.37 (s, 3H), 7.73(d, 2H), 8.53 (d, 2H), 8.66 (s, 2H).

Step B: Preparation of4,5-dimethyl-2-(4-trifluoromethylphenyl)pyrimidine

The title compound of Step A (9.0 g, 38 mmol) was dissolved in 50 mL oftetrahydrofuran and treated with methyl lithium (1.4 M in ether, 34 mL,47 mmol) at a temperature of −70° C. The reaction mixture exothermed to−35° C. The mixture was stirred at −30° C. for 1.5 h and then treatedwith 1 mL of water and dichlorodicyanoquinone (9.44 g, 42 mmol). Themixture was stirred at 25° C. for 30 minutes and then partitioned twicebetween 100 mL of water and 100 mL of dichloromethane. The combinedorganics were washed with brine and dried over magnesium sulfate. Theresidue after evaporation was subjected to silica gel chromatographyusing hexanes/ethyl acetate (95:5) as eluent to give 9.02 g of the titlecompound of Step B as a white solid melting at 128-131° C. ¹H NMR(CDCl₃): δ2.31 (s, 3H), 2.56 (s, 3H), 7.71 (d, 2H), 8.49 (d, 2H), 8.53(s, 1H).

Step C: Preparation of4-bromomethyl-5-methyl-2-(4-trifluoromethylphenyl)pyrimidine

The title compound of Step B (2.0 g, 8 mmol) was dissolved in 10 mL ofacetic acid and treated with bromine (0.4 mL, 8 mmol). The mixture washeated at 80° C. until the orange color was discharged (1 h). Themixture was evaporated under reduced pressure, diluted with 50 mL ofether and washed twice with 50 mL of sodium bicarbonate and then 50 mLof brine. The organic layer was dried over magnesium sulfate andconcentrated under reduced pressure to yield 2.54 g of the titlecompound of Step C as a tan solid which was used immediately in the nextstep without further purification. ¹H NMR (CDCl₃): δ2.44 (s, 3H), 4.54(s, 2H), 7.74 (d, 2H), 8.56 (d, 2H), 8.62 (s, 1H).

Step D: Preparation of5-methyl-2-(4-trifluoromethylphenyl)-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]methylpyrimidine

The title compound of Step C (0.7 g, 2 mmol), 3-trifluoromethylpyrazole(0.27 g, 2 mmol) and potassium carbonate (0.83 g, 6 mmol) were suspendedin 10 mL of acetonitrile and heated to reflux for 1 h. The salts werefiltered and the acetonitrile was removed under reduced pressure. Theresidue was purified by chromatography on silica gel eluting withhexanes/ethyl acetate (85:15) to afford 0.52 g of the title compound ofStep D, a compound of this invention, as a white solid melting at112-114° C. ¹H NMR (CDCl₃): δ2.39 (s, 3H), 5.53 (s, 2H), 6.62 (d, 1H),7.6-7.8 (m, 3H), 8.44 (d, 2H), 8.6 (s, 1H).

EXAMPLE 4 Step A: Preparation of(2-chloro-5-methyl-4-pyrimidinyl)[3-(trifluoromethyl)phenyl]methanone

2,4-Dichloro-5-methylpyrimidine (3.6 g, 18.4 mmol) was dissolved indichloromethane (50 mL) and treated sequentially with3-trifluoromethylbenzaldehyde (3.3 g, 18.4 mmol), and1,3-dimethylimidazolium iodide (1.37 g, 6.2 mmol). Sodium hydride (0.74g, 18.4 mmol) was added and an exotherm was noted. After being heated atreflux for 3 h, the reaction was quenched with water and the layers wereseparated. The dried (magnesium sulfate) organic layer was purified bychromatography on silica gel using hexanes/ethyl acetate 85:15 aseluent. The title compound of Step A (1.8 g) was isolated as a whitesolid melting at 113-116° C. ¹H NMR (CDCl₃/200 MHz) 2.39 (s, 3H), 7.66(m, 1H), 7.90 (d, 1H), 8.07 (s,1H), 8.69 (s, 1H).

Step B: Preparation of[5-methyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone

The title compound of Step A (0.6 g, 2 mmol), 3-trifluoromethylpyrazole(0.25 g), and potassium carbonate (0.8 g, 6 mmol) were suspended inacetonitrile (15 mL) and heated at reflux for 3 h. The cooled reactionmixture was filtered and the cake washed with acetonitrile. Afterevaporation of the solvent under reduced pressure, the residue wassubjected to silica gel chromatography using hexanes/ethyl acetate(85:15) to give 0.12 g of the title compound of Step B, a compound ofthe invention, as a white solid. ¹H NMR (CDCl₃/200 MHz) 2.45 (s, 3H),6.75 (d, 1H), 7.67 (d, 1H), 7.92 (d, 1H), 8.10 (s, 1H), 8.27 (s, 1H),8.54 (d, 1H), 8.9 (s, 1H).

EXAMPLE 5 Step A: Preparation of[5-methyl-2-[4-(trifluoromethyl)phenyl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone

The title compound of Example 1, Step A (0.6 g, 2 mmol),4-trifluoromethyl-benzeneboronic acid (1.1 g, 6 mmol), andbis(triphenylphosphine)palladium dichloride were dissolved indimethoxyethane (15 mL) and aqueous sodium carbonate (2 M, 4 mmol). Theresulting mixture was heated at 80° C. for 3 h. The mixture was dilutedwith dichloromethane (50 mL) and water (50 mL). The dichloromethanelayer was dried over magnesium sulfate, concentrated under reducedpressure, and the residue was subjected to silica gel chromatographyusing hexaneslethyl acetate (85:15). The title compound of Step A, acompound of the invention, was isolated as a white solid (0.56 g)melting at 159-161° C. ¹H NMR (CDCl₃/200 MHz) 2.47 (s, 3H), 7.62-7.78(m, 3H), 7.94 (d, 1H), 8.17 (d, 1H), 8.34 (s, 1H), 8.5 (d, 2H), 8.9 (s,1H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 34 can be prepared.

TABLE 1

R¹ R⁴ R⁵ R⁹ R¹ R⁴ R⁵ R⁹ R³ is H; X, Y and Z are CH H H CF₃ CF₃ H H OCF₃CF₃ H H CF₃ OCF₃ H H OCF₃ OCF₃ H H CF₃ SCF₃ H H OCF₃ SCF₃ H H CF₃ OCHF₂H H OCF₃ OCHF₂ H H CF₃ SCHF₂ H H OCF₃ SCHF₂ H H CF₃ C₂F₅ H H OCF₃ C₂F₅ HH CF₃ Cl H H OCF₃ Cl H H CF₃ SCH₂CH₃ H H OCF₃ SCH₂CH₃ H H OCHF₂ CF₃ H HSCF₃ CF₃ H H OCHF₂ OCF₃ H H SCF₃ OCF₃ H H OCHF₂ SCF₃ H H SCF₃ SCF₃ H HOCHF₂ OCHF₂ H H SCF₃ OCHF₂ H H OCHF₂ SCHF₂ H H SCF₃ SCHF₂ H H OCHF₂ C₂F₅H H SCF₃ C₂F₅ H H OCHF₂ Cl H H SCF₃ Cl H H OCHF₂ SCH₂CH₃ H H SCF₃SCH₂CH₃ H H SCHF₂ CF₃ H H Cl CF₃ H H SCHF₂ OCF₃ H H Cl OCF₃ H H SCHF₂SCF₃ H H Cl SCF₃ H H SCHF₂ OCHF₂ H H Cl OCHF₂ H H SCHF₂ SCHF₂ H H ClSCHF₂ H H SCHF₂ C₂F₅ H H Cl C₂F₅ H H SCHF₂ Cl H H Cl Cl H H SCHF₂SCH₂CH₃ H H Cl SCH₂CH₃ H CH₃ CF₃ CF₃ H CH₃ OCF₃ CF₃ H CH₃ CF₃ OCF₃ H CH₃OCF₃ OCF₃ H CH₃ CF₃ SCF₃ H CH₃ OCF₃ SCF₃ H CH₃ CF₃ OCHF₂ H CH₃ OCF₃OCHF₂ H CH₃ CF₃ SCHF₂ H CH₃ OCF₃ SCHF₂ H CH₃ CF₃ C₂F₅ H CH₃ OCF₃ C₂F₅ HCH₃ CF₃ Cl H CH₃ OCF₃ Cl H CH₃ CF₃ SCH₂CH₃ H CH₃ OCF₃ SCH₂CH₃ H CH₃OCHF₂ CF₃ H CH₃ SCF₃ CF₃ H CH₃ OCHF₂ OCF₃ H CH₃ SCF₃ OCF₃ H CH₃ OCHF₂SCF₃ H CH₃ SCF₃ SCF₃ H CH₃ OCHF₂ OCHF₂ H CH₃ SCF₃ OCHF₂ H CH₃ OCHF₂SCHF₂ H CH₃ SCF₃ SCHF₂ H CH₃ OCHF₂ C₂F₅ H CH₃ SCF₃ C₂F₅ H CH₃ OCHF₂ Cl HCH₃ SCF₃ Cl H CH₃ OCHF₂ SCH₂CH₃ H CH₃ SCF₃ SCH₂CH₃ H CH₃ SCHF₂ CF₃ H CH₃Cl CF₃ H CH₃ SCHF₂ OCF₃ H CH₃ Cl OCF₃ H CH₃ SCHF₂ SCF₃ H CH₃ Cl SCF₃ HCH₃ SCHF₂ OCHF₂ H CH₃ Cl OCHF₂ H CH₃ SCHF₂ SCHF₂ H CH₃ Cl SCHF₂ H CH₃SCHF₂ C₂F₅ H CH₃ Cl C₂F₅ H CH₃ SCHF₂ Cl H CH₃ Cl Cl H CH₃ SCHF₂ SCH₂CH₃H CH₃ Cl SCH₂CH₃ H F CF₃ CF₃ H F OCF₃ CF₃ H F CF₃ OCF₃ H F OCF₃ OCF₃ H FCF₃ SCF₃ H F OCF₃ SCF₃ H F CF₃ OCHF₂ H F OCF₃ OCHF₂ H F CF₃ SCHF₂ H FOCF₃ SCHF₂ H F CF₃ C₂F₅ H F OCF₃ C₂F₅ H F CF₃ Cl H F OCF₃ Cl H F CF₃SCH₂CH₃ H F OCF₃ SCH₂CH₃ H F OCHF₂ CF₃ H F SCF₃ OCF₃ H F OCHF₂ OCF₃ H FSCF₃ OCF₃ H F OCHF₂ SCF₃ H F SCF₃ SCF₃ H F OCHF₂ OCHF₂ H F SCF₃ OCHF₂ HF OCHF₂ SCHF₂ H F SCF₃ SCHF₂ H F OCHF₂ C₂F₅ H F SCF₃ C₂F₅ H F OCHF₂ Cl HF SCF₃ Cl H F OCHF₂ SCH₂CH₃ H F SCF₃ SCH₂CH₃ H F SCHF₂ CF₃ H F Cl CF₃ HF SCHF₂ OCF₃ H F Cl OCF₃ H F SCHF₂ SCF₃ H F Cl SCF₃ H F SCHF₂ OCHF₂ H FCl OCHF₂ H F SCHF₂ SCHF₂ H F Cl SCHF₂ H F SCHF₂ C₂F₅ H F Cl C₂F₅ H FSCHF₂ Cl H F Cl Cl H F SCHF₂ SCH₂CH₃ H F Cl SCH₂CH₃ H Cl CF₃ CF₃ H ClOCF₃ CF₃ H Cl CF₃ OCF₃ H Cl OCF₃ OCF₃ H Cl CF₃ SCF₃ H Cl OCF₃ SCF₃ H ClCF₃ OCHF₂ H Cl OCF₃ OCHF₂ H Cl CF₃ SCHF₂ H Cl OCF₃ SCHF₂ H Cl CF₃ C₂F₅ HCl OCF₃ C₂F₅ H Cl CF₃ Cl H Cl OCF₃ Cl H Cl CF₃ SCH₂CH₃ H Cl OCF₃ SCH₂CH₃H Cl OCHF₂ CF₃ H Cl SCF₃ CF₃ H Cl OCHF₂ OCF₃ H Cl SCF₃ OCF₃ H Cl OCHF₂SCF₃ H Cl SCF₃ SCF₃ H Cl OCHF₂ OCHF₂ H Cl SCF₃ OCHF₂ H Cl OCHF₂ SCHF₂ HCl SCF₃ SCHF₂ H Cl OCHF₂ C₂F₅ H Cl SCF₃ C₂F₅ H Cl OCHF₂ Cl H Cl SCF₃ ClH Cl OCHF₂ SCH₂CH₃ H Cl SCF₃ SCH₂CH₃ H Cl SCHF₂ CF₃ H Cl Cl CF₃ H ClSCHF₂ OCF₃ H Cl Cl OCF₃ H Cl SCHF₂ SCF₃ H Cl Cl SCF₃ H Cl SCHF₂ OCHF₂ HCl Cl OCHF₂ H Cl SCHF₂ SCHF₂ H Cl Cl SCHF₂ H Cl SCHF₂ C₂F₅ H Cl Cl C₂F₅H Cl SCHF₂ Cl H Cl Cl Cl H Cl SCHF₂ SCH₂CH₃ H Cl Cl SCH₂CH₃ CH₃ H CF₃CF₃ CH₃ H OCF₃ CF₃ CH₃ H CF₃ OCF₃ CH₃ H OCF₃ OCF₃ CH₃ H CF₃ SCF₃ CH₃ HOCF₃ SCF₃ CH₃ H CF₃ OCHF₂ CH₃ H OCF₃ OCHF₂ CH₃ H CF₃ SCHF₂ CH₃ H OCF₃SCHF₂ CH₃ H CF₃ C₂F₅ CH₃ H OCF₃ C₂F₅ CH₃ H CF₃ Cl CH₃ H OCF₃ Cl CH₃ HCF₃ SCH₂CH₃ CH₃ H OCF₃ SCH₂CH₃ CH₃ H OCHF₂ CF₃ CH₃ H SCF₃ CF₃ CH₃ HOCHF₂ OCF₃ CH₃ H SCF₃ OCF₃ CH₃ H OCHF₂ SCF₃ CH₃ H SCF₃ SCF₃ CH₃ H OCHF₂OCHF₂ CH₃ H SCF₃ OCHF₂ CH₃ H OCHF₂ SCHF₂ CH₃ H SCF₃ SCHF₂ CH₃ H OCHF₂C₂F₅ CH₃ H SCF₃ C₂F₅ CH₃ H OCHF₂ Cl CH₃ H SCF₃ Cl CH₃ H OCHF₂ SCH₂CH₃CH₃ H SCF₃ SCH₂CH₃ CH₃ H SCHF₂ CF₃ CH₃ H Cl CF₃ CH₃ H SCHF₂ OCF₃ CH₃ HCl OCF₃ CH₃ H SCHF₂ SCF₃ CH₃ H Cl SCF₃ CH₃ H SCHF₂ OCHF₂ CH₃ H Cl OCHF₂CH₃ H SCHF₂ SCHF₂ CH₃ H Cl SCHF₂ CH₃ H SCHF₂ C₂F₅ CH₃ H Cl C₂F₅ CH₃ HSCHF₂ Cl CH₃ H Cl Cl CH₃ H SCHF₂ SCH₂CH₃ CH₃ H Cl SCH₂CH₃ CH₃ CH₃ CF₃CF₃ CH₃ CH₃ OCF₃ CF₃ CH₃ CH₃ CF₃ OCF₃ CH₃ CH₃ OCF₃ OCF₃ CH₃ CH₃ CF₃ SCF₃CH₃ CH₃ OCF₃ SCF₃ CH₃ CH₃ CF₃ OCHF₂ CH₃ CH₃ OCF₃ OCHF₂ CH₃ CH₃ CF₃ SCHF₂CH₃ CH₃ OCF₃ SCHF₂ CH₃ CH₃ CF₃ C₂F₅ CH₃ CH₃ OCF₃ C₂F₅ CH₃ CH₃ CF₃ Cl CH₃CH₃ OCF₃ Cl CH₃ CH₃ CF₃ SCH₂CH₃ CH₃ CH₃ OCF₃ SCH₂CH₃ CH₃ CH₃ OCHF₂ CF₃CH₃ CH₃ SCF₃ CF₃ CH₃ CH₃ OCHF₂ OCF₃ CH₃ CH₃ SCF₃ OCF₃ CH₃ CH₃ OCHF₂ SCF₃CH₃ CH₃ SCF₃ SCF₃ CH₃ CH₃ OCHF₂ OCHF₂ CH₃ CH₃ SCF₃ OCHF₂ CH₃ CH₃ OCHF₂SCHF₂ CH₃ CH₃ SCF₃ SCHF₂ CH₃ CH₃ OCHF₂ C₂F₅ CH₃ CH₃ SCF₃ C₂F₅ CH₃ CH₃OCHF₂ Cl CH₃ CH₃ SCF₃ Cl CH₃ CH₃ OCHF₂ SCH₂CH₃ CH₃ CH₃ SCF₃ SCH₂CH₃ CH₃CH₃ SCHF₂ CF₃ CH₃ CH₃ Cl CF₃ CH₃ CH₃ SCHF₂ OCF₃ CH₃ CH₃ Cl OCF₃ CH₃ CH₃SCHF₂ SCF₃ CH₃ CH₃ Cl SCF₃ CH₃ CH₃ SCHF₂ OCHF₂ CH₃ CH₃ Cl OCHF₂ CH₃ CH₃SCHF₂ SCHF₂ CH₃ CH₃ Cl SCHF₂ CH₃ CH₃ SCHF₂ C₂F₅ CH₃ CH₃ Cl C₂F₅ CH₃ CH₃SCHF₂ Cl CH₃ CH₃ Cl Cl CH₃ CH₃ SCHF₂ SCH₂CH₃ CH₃ CH₃ Cl SCH₂CH₃ CH₃ FCF₃ CF₃ CH₃ F OCF₃ CF₃ CH₃ F CF₃ OCF₃ CH₃ F OCF₃ OCF₃ CH₃ F CF₃ SCF₃ CH₃F OCF₃ SCF₃ CH₃ F CF₃ OCHF₂ CH₃ F OCF₃ OCHF₂ CH₃ F CF₃ SCHF₂ CH₃ F OCF₃SCHF₂ CH₃ F CF₃ C₂F₅ CH₃ F OCF₃ C₂F₅ CH₃ F CF₃ Cl CH₃ F OCF₃ Cl CH₃ FCF₃ SCH₂CH₃ CH₃ F OCF₃ SCH₂CH₃ CH₃ F OCHF₂ CF₃ CH₃ F SCF₃ CF₃ CH₃ FOCHF₂ OCF₃ CH₃ F SCF₃ OCF₃ CH₃ F OCHF₂ SCF₃ CH₃ F SCF₃ SCF₃ CH₃ F OCHF₂OCHF₂ CH₃ F SCF₃ OCHF₂ CH₃ F OCHF₂ SCHF₂ CH₃ F SCF₃ SCHF₂ CH₃ F OCHF₂C₂F₅ CH₃ F SCF₃ C₂F₅ CH₃ F OCHF₂ Cl CH₃ F SCF₃ Cl CH₃ F OCHF₂ SCH₂CH₃CH₃ F SCF₃ SCH₂CH₃ CH₃ F SCHF₂ CF₃ CH₃ F Cl CF₃ CH₃ F SCHF₂ OCF₃ CH₃ FCl OCF₃ CH₃ F SCHF₂ SCF₃ CH₃ F Cl SCF₃ CH₃ F SCHF₂ OCHF₂ CH₃ F Cl OCHF₂CH₃ F SCHF₂ SCHF₂ CH₃ F Cl SCHF₂ CH₃ F SCHF₂ C₂F₅ CH₃ F Cl C₂F₅ CH₃ FSCHF₂ Cl CH₃ F Cl Cl CH₃ F SCHF₂ SCH₂CH₃ CH₃ F Cl SCH₂CH₃ CH₃ Cl CF₃ CF₃CH₃ Cl OCF₃ CF₃ CH₃ Cl CF₃ OCF₃ CH₃ Cl OCF₃ OCF₃ CH₃ Cl CF₃ SCF₃ CH₃ ClOCF₃ SCF₃ CH₃ Cl CF₃ OCHF₂ CH₃ Cl OCF₃ OCHF₂ CH₃ Cl CF₃ SCHF₂ CH₃ ClOCF₃ SCHF₂ CH₃ Cl CF₃ C₂F₅ CH₃ Cl OCF₃ C₂F₅ CH₃ Cl CF₃ Cl CH₃ Cl OCF₃ ClCH₃ Cl CF₃ SCH₂CH₃ CH₃ Cl OCF₃ SCH₂CH₃ CH₃ Cl OCHF₂ CF₃ CH₃ Cl SCF₃ CF₃CH₃ Cl OCHF₂ OCF₃ CH₃ Cl SCF₃ OCF₃ CH₃ Cl OCHF₂ SCF₃ CH₃ Cl SCF₃ SCF₃CH₃ Cl OCHF₂ OCHF₂ CH₃ Cl SCF₃ OCHF₂ CH₃ Cl OCHF₂ SCHF₂ CH₃ Cl SCF₃SCHF₂ CH₃ Cl OCHF₂ C₂F₅ CH₃ Cl SCF₃ C₂F₅ CH₃ Cl OCHF₂ Cl CH₃ Cl SCF₃ ClCH₃ Cl OCHF₂ SCH₂CH₃ CH₃ Cl SCF₃ SCH₂CH₃ CH₃ Cl SCHF₂ CF₃ CH₃ Cl Cl CF₃CH₃ Cl SCHF₂ OCF₃ CH₃ Cl Cl OCF₃ CH₃ Cl SCHF₂ SCF₃ CH₃ Cl Cl SCF₃ CH₃ ClSCHF₂ OCHF₂ CH₃ Cl Cl OCHF₂ CH₃ Cl SCHF₂ SCHF₂ CH₃ Cl Cl SCHF₂ CH₃ ClSCHF₂ C₂F₅ CH₃ Cl Cl C₂F₅ CH₃ Cl SCHF₂ Cl CH₃ Cl Cl Cl CH₃ Cl SCHF₂SCH₂CH₃ CH₃ Cl Cl SCH₂CH₃ OCH₃ H CF₃ CF₃ OCH₃ H OCF₃ CF₃ OCH₃ H CF₃ OCF₃OCH₃ H OCF₃ OCF₃ OCH₃ H CF₃ SCF₃ OCH₃ H OCF₃ SCF₃ OCH₃ H CF₃ OCHF₂ OCH₃H OCF₃ OCHF₂ OCH₃ H CF₃ SCHF₂ OCH₃ H OCF₃ SCHF₂ OCH₃ H CF₃ C₂F₅ OCH₃ HOCF₃ C₂F₅ OCH₃ H CF₃ Cl OCH₃ H OCF₃ Cl OCH₃ H CF₃ SCH₂CH₃ OCH₃ H OCF₃SCH₂CH₃ OCH₃ H OCHF₂ CF₃ OCH₃ H SCF₃ CF₃ OCH₃ H OCHF₂ OCF₃ OCH₃ H SCF₃OCF₃ OCH₃ H OCHF₂ SCF₃ OCH₃ H SCF₃ SCF₃ OCH₃ H OCHF₂ OCHF₂ OCH₃ H SCF₃OCHF₂ OCH₃ H OCHF₂ SCHF₂ OCH₃ H SCF₃ SCHF₂ OCH₃ H OCHF₂ C₂F₅ OCH₃ H SCF₃C₂F₅ OCH₃ H OCHF₂ Cl OCH₃ H SCF₃ Cl OCH₃ H OCHF₂ SCH₂CH₃ OCH₃ H SCF₃SCH₂CH₃ OCH₃ H SCHF₂ CF₃ OCH₃ H Cl CF₃ OCH₃ H SCHF₂ OCF₃ OCH₃ H Cl OCF₃OCH₃ H SCHF₂ SCF₃ OCH₃ H Cl SCF₃ OCH₃ H SCHF₂ OCHF₂ OCH₃ H Cl OCHF₂ OCH₃H SCHF₂ SCHF₂ OCH₃ H Cl SCHF₂ OCH₃ H SCHF₂ C₂F₅ OCH₃ H Cl C₂F₅ OCH₃ HSCHF₂ Cl OCH₃ H Cl Cl OCH₃ H SCHF₂ SCH₂CH₃ OCH₃ H Cl SCH₂CH₃ OCH₃ CH₃CF₃ CF₃ OCH₃ CH₃ OCF₃ CF₃ OCH₃ CH₃ CF₃ OCF₃ OCH₃ CH₃ OCF₃ OCF₃ OCH₃ CH₃CF₃ SCF₃ OCH₃ CH₃ OCF₃ SCF₃ OCH₃ CH₃ CF₃ OCHF₂ OCH₃ CH₃ OCF₃ OCHF₂ OCH₃CH₃ CF₃ SCHF₂ OCH₃ CH₃ OCF₃ SCHF₂ OCH₃ CH₃ CF₃ C₂F₅ OCH₃ CH₃ OCF₃ C₂F₅OCH₃ CH₃ CF₃ Cl OCH₃ CH₃ OCF₃ Cl OCH₃ CH₃ CF₃ SCH₂CH₃ OCH₃ CH₃ OCF₃SCH₂CH₃ OCH₃ CH₃ OCHF₂ CF₃ OCH₃ CH₃ SCF₃ CF₃ OCH₃ CH₃ OCHF₂ OCF₃ OCH₃CH₃ SCF₃ OCF₃ OCH₃ CH₃ OCHF₂ SCF₃ OCH₃ CH₃ SCF₃ SCF₃ OCH₃ CH₃ OCHF₂OCHF₂ OCH₃ CH₃ SCF₃ OCHF₂ OCH₃ CH₃ OCHF₂ SCHF₂ OCH₃ CH₃ SCF₃ SCHF₂ OCH₃CH₃ OCHF₂ C₂F₅ OCH₃ CH₃ SCF₃ C₂F₅ OCH₃ CH₃ OCHF₂ Cl OCH₃ CH₃ SCF₃ ClOCH₃ CH₃ OCHF₂ SCH₂CH₃ OCH₃ CH₃ SCF₃ SCH₂CH₃ OCH₃ CH₃ SCHF₂ CF₃ OCH₃ CH₃Cl CF₃ OCH₃ CH₃ SCHF₂ OCF₃ OCH₃ CH₃ Cl OCF₃ OCH₃ CH₃ SCHF₂ SCF₃ OCH₃ CH₃Cl SCF₃ OCH₃ CH₃ SCHF₂ OCHF₂ OCH₃ CH₃ Cl OCHF₂ OCH₃ CH₃ SCHF₂ SCHF₂ OCH₃CH₃ Cl SCHF₂ OCH₃ CH₃ SCHF₂ C₂F₅ OCH₃ CH₃ Cl C₂F₅ OCH₃ CH₃ SCHF₂ Cl OCH₃CH₃ Cl Cl OCH₃ CH₃ SCHF₂ SCH₂CH₃ OCH₃ CH₃ Cl SCH₂CH₃ OCH₃ F CF₃ CF₃ OCH₃F OCF₃ CF₃ OCH₃ F CF₃ OCF₃ OCH₃ F OCF₃ OCF₃ OCH₃ F CF₃ SCF₃ OCH₃ F OCF₃SCF₃ OCH₃ F CF₃ OCHF₂ OCH₃ F OCF₃ OCHF₂ OCH₃ F CF₃ SCHF₂ OCH₃ F OCF₃SCHF₂ OCH₃ F CF₃ C₂F₅ OCH₃ F OCF₃ C₂F₅ OCH₃ F CF₃ Cl OCH₃ F OCF₃ Cl OCH₃F CF₃ SCH₂CH₃ OCH₃ F OCF₃ SCH₂CH₃ OCH₃ F OCHF₂ CF₃ OCH₃ F SCF₃ CF₃ OCH₃F OCHF₂ OCF₃ OCH₃ F SCF₃ OCF₃ OCH₃ F OCHF₂ SCF₃ OCH₃ F SCF₃ SCF₃ OCH₃ FOCHF₂ OCHF₂ OCH₃ F SCF₃ OCHF₂ OCH₃ F OCHF₂ SCHF₂ OCH₃ F SCF₃ SCHF₂ OCH₃F OCHF₂ C₂F₅ OCH₃ F SCF₃ C₂F₅ OCH₃ F OCHF₂ Cl OCH₃ F SCF₃ Cl OCH₃ FOCHF₂ SCH₂CH₃ OCH₃ F SCF₃ SCH₂CH₃ OCH₃ F SCHF₂ CF₃ OCH₃ F Cl CF₃ OCH₃ FSCHF₂ OCF₃ OCH₃ F Cl OCF₃ OCH₃ F SCHF₂ SCF₃ OCH₃ F Cl SCF₃ OCH₃ F SCHF₂OCHF₂ OCH₃ F Cl OCHF₂ OCH₃ F SCHF₂ SCHF₂ OCH₃ F Cl SCHF₂ OCH₃ F SCHF₂C₂F₅ OCH₃ F Cl C₂F₅ OCH₃ F SCHF₂ Cl OCH₃ F Cl Cl OCH₃ F SCHF₂ SCH₂CH₃OCH₃ F Cl SCH₂CH₃ OCH₃ Cl CF₃ CF₃ OCH₃ Cl OCF₃ CF₃ OCH₃ Cl CF₃ OCF₃ OCH₃Cl OCF₃ OCF₃ OCH₃ Cl CF₃ SCF₃ OCH₃ Cl OCF₃ SCF₃ OCH₃ Cl CF₃ OCHF₂ OCH₃Cl OCF₃ OCHF₂ OCH₃ Cl CF₃ SCHF₂ OCH₃ Cl OCF₃ SCHF₂ OCH₃ Cl CF₃ C₂F₅ OCH₃Cl OCF₃ C₂F₅ OCH₃ Cl CF₃ Cl OCH₃ Cl OCF₃ Cl OCH₃ Cl CF₃ SCH₂CH₃ OCH₃ ClOCF₃ SCH₂CH₃ OCH₃ Cl OCHF₂ CF₃ OCH₃ Cl SCF₃ CF₃ OCH₃ Cl OCHF₂ OCF₃ OCH₃Cl SCF₃ OCF₃ OCH₃ Cl OCHF₂ SCF₃ OCH₃ Cl SCF₃ SCF₃ OCH₃ Cl OCHF₂ OCHF₂OCH₃ Cl SCF₃ OCHF₂ OCH₃ Cl OCHF₂ SCHF₂ OCH₃ Cl SCF₃ SCHF₂ OCH₃ Cl OCHF₂C₂F₅ OCH₃ Cl SCF₃ C₂F₅ OCH₃ Cl OCHF₂ Cl OCH₃ Cl SCF₃ Cl OCH₃ Cl OCHF₂SCH₂CH₃ OCH₃ Cl SCF₃ SCH₂CH₃ OCH₃ Cl SCHF₂ CF₃ OCH₃ Cl Cl CF₃ OCH₃ ClSCHF₂ OCF₃ OCH₃ Cl Cl OCF₃ OCH₃ Cl SCHF₂ SCF₃ OCH₃ Cl Cl SCF₃ OCH₃ ClSCHF₂ OCHF₂ OCH₃ Cl Cl OCHF₂ OCH₃ Cl SCHF₂ SCHF₂ OCH₃ Cl Cl SCHF₂ OCH₃Cl SCHF₂ C₂F₅ OCH₃ Cl Cl C₂F₅ OCH₃ Cl SCHF₂ Cl OCH₃ Cl Cl Cl OCH₃ ClSCHF₂ SCH₂CH₃ OCH₃ Cl Cl SCH₂CH₃ CH₂CH₃ H CF₃ CF₃ CH₂CH₃ H OCF₃ CF₃CH₂CH₃ H CF₃ OCF₃ CH₂CH₃ H OCF₃ OCF₃ CH₂CH₃ H CF₃ SCF₃ CH₂CH₃ H OCF₃SCF₃ CH₂CH₃ H CF₃ OCHF₂ CH₂CH₃ H OCF₃ OCHF₂ CH₂CH₃ H CF₃ SCHF₂ CH₂CH₃ HOCF₃ SCHF₂ CH₂CH₃ H CF₃ C₂F₅ CH₂CH₃ H OCF₃ C₂F₅ CH₂CH₃ H CF₃ Cl CH₂CH₃ HOCF₃ Cl CH₂CH₃ H CF₃ SCH₂CH₃ CH₂CH₃ H OCF₃ SCH₂CH₃ CH₂CH₃ H OCHF₂ CF₃CH₂CH₃ H SCF₃ CF₃ CH₂CH₃ H OCHF₂ OCF₃ CH₂CH₃ H SCF₃ OCF₃ CH₂CH₃ H OCHF₂SCF₃ CH₂CH₃ H SCF₃ SCF₃ CH₂CH₃ H OCHF₂ OCHF₂ CH₂CH₃ H SCF₃ OCHF₂ CH₂CH₃H OCHF₂ SCHF₂ CH₂CH₃ H SCF₃ SCHF₂ CH₂CH₃ H OCHF₂ C₂F₅ CH₂CH₃ H SCF₃ C₂F₅CH₂CH₃ H OCHF₂ Cl CH₂CH₃ H SCF₃ Cl CH₂CH₃ H OCHF₂ SCH₂CH₃ CH₂CH₃ H SCF₃SCH₂CH₃ CH₂CH₃ H SCHF₂ CF₃ CH₂CH₃ H Cl CF₃ CH₂CH₃ H SCHF₂ OCF₃ CH₂CH₃ HCl OCF₃ CH₂CH₃ H SCHF₂ SCF₃ CH₂CH₃ H Cl SCF₃ CH₂CH₃ H SCHF₂ OCHF₂ CH₂CH₃H Cl OCHF₂ CH₂CH₃ H SCHF₂ SCHF₂ CH₂CH₃ H Cl SCHF₂ CH₂CH₃ H SCHF₂ C₂F₅CH₂CH₃ H Cl C₂F₅ CH₂CH₃ H SCHF₂ Cl CH₂CH₃ H Cl Cl CH₂CH₃ H SCHF₂ SCH₂CH₃CH₂CH₃ H Cl SCH₂CH₃ CH₂CH₃ CH₃ CF₃ CF₃ CH₂CH₃ CH₃ OCF₃ CF₃ CH₂CH₃ CH₃CF₃ OCF₃ CH₂CH₃ CH₃ OCF₃ OCF₃ CH₂CH₃ CH₃ CF₃ SCF₃ CH₂CH₃ CH₃ OCF₃ SCF₃CH₂CH₃ CH₃ CF₃ OCHF₂ CH₂CH₃ CH₃ OCF₃ OCHF₂ CH₂CH₃ CH₃ CF₃ SCHF₂ CH₂CH₃CH₃ OCF₃ SCHF₂ CH₂CH₃ CH₃ CF₃ C₂F₅ CH₂CH₃ CH₃ OCF₃ C₂F₅ CH₂CH₃ CH₃ CF₃Cl CH₂CH₃ CH₃ OCF₃ Cl CH₂CH₃ CH₃ CF₃ SCH₂CH₃ CH₂CH₃ CH₃ OCF₃ SCH₂CH₃CH₂CH₃ CH₃ OCHF₂ CF₃ CH₂CH₃ CH₃ SCF₃ CF₃ CH₂CH₃ CH₃ OCHF₂ OCF₃ CH₂CH₃CH₃ SCF₃ OCF₃ CH₂CH₃ CH₃ OCHF₂ SCF₃ CH₂CH₃ CH₃ SCF₃ SCF₃ CH₂CH₃ CH₃OCHF₂ OCHF₂ CH₂CH₃ CH₃ SCF₃ OCHF₂ CH₂CH₃ CH₃ OCHF₂ SCHF₂ CH₂CH₃ CH₃ SCF₃SCHF₂ CH₂CH₃ CH₃ OCHF₂ C₂F₅ CH₂CH₃ CH₃ SCF₃ C₂F₅ CH₂CH₃ CH₃ OCHF₂ ClCH₂CH₃ CH₃ SCF₃ Cl CH₂CH₃ CH₃ OCHF₂ SCH₂CH₃ CH₂CH₃ CH₃ SCF₃ SCH₂CH₃CH₂CH₃ CH₃ SCHF₂ CF₃ CH₂CH₃ CH₃ Cl CF₃ CH₂CH₃ CH₃ SCHF₂ OCF₃ CH₂CH₃ CH₃Cl OCF₃ CH₂CH₃ CH₃ SCHF₂ SCF₃ CH₂CH₃ CH₃ Cl SCF₃ CH₂CH₃ CH₃ SCHF₂ OCHF₂CH₂CH₃ CH₃ Cl OCHF₂ CH₂CH₃ CH₃ SCHF₂ SCHF₂ CH₂CH₃ CH₃ Cl SCHF₂ CH₂CH₃CH₃ SCHF₂ C₂F₅ CH₂CH₃ CH₃ Cl C₂F₅ CH₂CH₃ CH₃ SCHF₂ Cl CH₂CH₃ CH₃ Cl ClCH₂CH₃ CH₃ SCHF₂ SCH₂CH₃ CH₂CH₃ CH₃ Cl SCH₂CH₃ CH₂CH₃ F CF₃ CF₃ CH₂CH₃ FOCF₃ CF₃ CH₂CH₃ F CF₃ OCF₃ CH₂CH₃ F OCF₃ OCF₃ CH₂CH₃ F CF₃ SCF₃ CH₂CH₃ FOCF₃ SCF₃ CH₂CH₃ F CF₃ OCHF₂ CH₂CH₃ F OCF₃ OCHF₂ CH₂CH₃ F CF₃ SCHF₂CH₂CH₃ F OCF₃ SCHF₂ CH₂CH₃ F CF₃ C₂F₅ CH₂CH₃ F OCF₃ C₂F₅ CH₂CH₃ F CF₃ ClCH₂CH₃ F OCF₃ Cl CH₂CH₃ F CF₃ SCH₂CH₃ CH₂CH₃ F OCF₃ SCH₂CH₃ CH₂CH₃ FOCHF₂ CF₃ CH₂CH₃ F SCF₃ CF₃ CH₂CH₃ F OCHF₂ OCF₃ CH₂CH₃ F SCF₃ OCF₃CH₂CH₃ F OCHF₂ SCF₃ CH₂CH₃ F SCF₃ SCF₃ CH₂CH₃ F OCHF₂ OCHF₂ CH₂CH₃ FSCF₃ OCHF₂ CH₂CH₃ F OCHF₂ SCHF₂ CH₂CH₃ F SCF₃ SCHF₂ CH₂CH₃ F OCHF₂ C₂F₅CH₂CH₃ F SCF₃ C₂F₅ CH₂CH₃ F OCHF₂ Cl CH₂CH₃ F SCF₃ Cl CH₂CH₃ F OCHF₂SCH₂CH₃ CH₂CH₃ F SCF₃ SCH₂CH₃ CH₂CH₃ F SCHF₂ CF₃ CH₂CH₃ F Cl CF₃ CH₂CH₃F SCHF₂ OCF₃ CH₂CH₃ F Cl OCF₃ CH₂CH₃ F SCHF₂ SCF₃ CH₂CH₃ F Cl SCF₃CH₂CH₃ F SCHF₂ OCHF₂ CH₂CH₃ F Cl OCHF₂ CH₂CH₃ F SCHF₂ SCHF₂ CH₂CH₃ F ClSCHF₂ CH₂CH₃ F SCHF₂ C₂F₅ CH₂CH₃ F Cl C₂F₅ CH₂CH₃ F SCHF₂ Cl CH₂CH₃ F ClCl CH₂CH₃ F SCHF₂ SCH₂CH₃ CH₂CH₃ F Cl SCH₂CH₃ CH₂CH₃ Cl CF₃ CF₃ CH₂CH₃Cl OCF₃ CF₃ CH₂CH₃ Cl CF₃ OCF₃ CH₂CH₃ Cl OCF₃ OCF₃ CH₂CH₃ Cl CF₃ SCF₃CH₂CH₃ Cl OCF₃ SCF₃ CH₂CH₃ Cl CF₃ OCHF₂ CH₂CH₃ Cl OCF₃ OCHF₂ CH₂CH₃ ClCF₃ SCHF₂ CH₂CH₃ Cl OCF₃ SCHF₂ CH₂CH₃ Cl CF₃ C₂F₅ CH₂CH₃ Cl OCF₃ C₂F₅CH₂CH₃ Cl CF₃ Cl CH₂CH₃ Cl OCF₃ Cl CH₂CH₃ Cl CF₃ SCH₂CH₃ CH₂CH₃ Cl OCF₃SCH₂CH₃ CH₂CH₃ Cl OCHF₂ CF₃ CH₂CH₃ Cl SCF₃ CF₃ CH₂CH₃ Cl OCHF₂ OCF₃CH₂CH₃ Cl SCF₃ OCF₃ CH₂CH₃ Cl OCHF₂ SCF₃ CH₂CH₃ Cl SCF₃ SCF₃ CH₂CH₃ ClOCHF₂ OCHF₂ CH₂CH₃ Cl SCF₃ OCHF₂ CH₂CH₃ Cl OCHF₂ SCHF₂ CH₂CH₃ Cl SCF₃SCHF₂ CH₂CH₃ Cl OCHF₂ C₂F₅ CH₂CH₃ Cl SCF₃ C₂F₅ CH₂CH₃ Cl OCHF₂ Cl CH₂CH₃Cl SCF₃ Cl CH₂CH₃ Cl OCHF₂ SCH₂CH₃ CH₂CH₃ Cl SCF₃ SCH₂CH₃ CH₂CH₃ ClSCHF₂ CF₃ CH₂CH₃ Cl Cl CF₃ CH₂CH₃ Cl SCHF₂ OCF₃ CH₂CH₃ Cl Cl OCF₃ CH₂CH₃Cl SCHF₂ SCF₃ CH₂CH₃ Cl Cl SCF₃ CH₂CH₃ Cl SCHF₂ OCHF₂ CH₂CH₃ Cl Cl OCHF₂CH₂CH₃ Cl SCHF₂ SCHF₂ CH₂CH₃ Cl Cl SCHF₂ CH₂CH₃ Cl SCHF₂ C₂F₅ CH₂CH₃ ClCl C₂F₅ CH₂CH₃ Cl SCHF₂ Cl CH₂CH₃ Cl Cl Cl CH₂CH₃ Cl SCHF₂ SCH₂CH₃CH₂CH₃ Cl Cl SCH₂CH₃ R³ is F H F CF₃ CF₃ H F OCF₃ CF₃ H F CF₃ OCF₃ H FOCF₃ OCF₃ H F CF₃ SCF₃ H F OCF₃ SCF₃ H F CF₃ OCHF₂ H F OCF₃ OCHF₂ H FCF₃ SCHF₂ H F OCF₃ SCHF₂ H F CF₃ C₂F₅ H F OCF₃ C₂F₅ H F CF₃ Cl H F OCF₃Cl H F CF₃ SCH₂CH₃ H F OCF₃ SCH₂CH₃ H F OCHF₂ CF₃ H F SCF₃ CF₃ H F OCHF₂OCF₃ H F SCF₃ OCF₃ H F OCHF₂ SCF₃ H F SCF₃ SCF₃ H F OCHF₂ OCHF₂ H F SCF₃OCHF₂ H F OCHF₂ SCHF₂ H F SCF₃ SCHF₂ H F OCHF₂ C₂F₅ H F SCF₃ C₂F₅ H FOCHF₂ Cl H F SCF₃ Cl H F OCHF₂ SCH₂CH₃ H F SCF₃ SCH₂CH₃ H F SCHF₂ CF₃ HF Cl CF₃ H F SCHF₂ OCF₃ H F Cl OCF₃ H F SCHF₂ SCF₃ H F Cl SCF₃ H F SCHF₂OCHF₂ H F Cl OCHF₂ H F SCHF₂ SCHF₂ H F Cl SCHF₂ H F SCHF₂ C₂F₅ H F ClC₂F₅ H F SCHF₂ Cl H F Cl Cl H F SCHF₂ SCH₂CH₃ H F Cl SCH₂CH₃ CH₃ F CF₃CF₃ CH₃ F OCF₃ CF₃ CH₃ F CF₃ OCF₃ CH₃ F OCF₃ OCF₃ CH₃ F CF₃ SCF₃ CH₃ FOCF₃ SCF₃ CH₃ F CF₃ OCHF₂ CH₃ F OCF₃ OCHF₂ CH₃ F CF₃ SCHF₂ CH₃ F OCF₃SCHF₂ CH₃ F CF₃ C₂F₅ CH₃ F OCF₃ C₂F₅ CH₃ F CF₃ Cl CH₃ F OCF₃ Cl CH₃ FCF₃ SCH₂CH₃ CH₃ F OCF₃ SCH₂CH₃ CH₃ F OCHF₂ CF₃ CH₃ F SCF₃ CF₃ CH₃ FOCHF₂ OCF₃ CH₃ F SCF₃ OCF₃ CH₃ F OCHF₂ SCF₃ CH₃ F SCF₃ SCF₃ CH₃ F OCHF₂OCHF₂ CH₃ F SCF₃ OCHF₂ CH₃ F OCHF₂ SCHF₂ CH₃ F SCF₃ SCHF₂ CH₃ F OCHF₂C₂F₅ CH₃ F SCF₃ C₂F₅ CH₃ F OCHF₂ Cl CH₃ F SCF₃ Cl CH₃ F OCHF₂ SCH₂CH₃CH₃ F SCF₃ SCH₂CH₃ CH₃ F SCHF₂ CF₃ CH₃ F Cl CF₃ CH₃ F SCHF₂ OCF₃ CH₃ FCl OCF₃ CH₃ F SCHF₂ SCF₃ CH₃ F Cl SCF₃ CH₃ F SCHF₂ OCHF₂ CH₃ F Cl OCHF₂CH₃ F SCHF₂ SCHF₂ CH₃ F Cl SCHF₂ CH₃ F SCHF₂ C₂F₅ CH₃ F Cl C₂F₅ CH₃ FSCHF₂ Cl CH₃ F Cl Cl CH₃ F SCHF₂ SCH₂CH₃ CH₃ F Cl SCH₂CH₃ OCH₃ F CF₃ CF₃OCH₃ F OCF₃ CF₃ OCH₃ F CF₃ OCF₃ OCH₃ F OCF₃ OCF₃ OCH₃ F CF₃ SCF₃ OCH₃ FOCF₃ SCF₃ OCH₃ F CF₃ OCHF₂ OCH₃ F OCF₃ OCHF₂ OCH₃ F CF₃ SCHF₂ OCH₃ FOCF₃ SCHF₂ OCH₃ F CF₃ C₂F₅ OCH₃ F OCF₃ C₂F₅ OCH₃ F CF₃ Cl OCH₃ F OCF₃ ClOCH₃ F CF₃ SCH₂CH₃ OCH₃ F OCF₃ SCH₂CH₃ OCH₃ F OCHF₂ CF₃ OCH₃ F SCF₃ CF₃OCH₃ F OCHF₂ OCF₃ OCH₃ F SCF₃ OCF₃ OCH₃ F OCHF₂ SCF₃ OCH₃ F SCF₃ SCF₃OCH₃ F OCHF₂ OCHF₂ OCH₃ F SCF₃ OCHF₂ OCH₃ F OCHF₂ SCHF₂ OCH₃ F SCF₃SCHF₂ OCH₃ F OCHF₂ C₂F₅ OCH₃ F SCF₃ C₂F₅ OCH₃ F OCHF₂ Cl OCH₃ F SCF₃ ClOCH₃ F OCHF₂ SCH₂CH₃ OCH₃ F SCF₃ SCH₂CH₃ OCH₃ F SCHF₂ CF₃ OCH₃ F Cl CF₃OCH₃ F SCHF₂ OCF₃ OCH₃ F Cl OCF₃ OCH₃ F SCHF₂ SCF₃ OCH₃ F Cl SCF₃ OCH₃ FSCHF₂ OCHF₂ OCH₃ F Cl OCHF₂ OCH₃ F SCHF₂ SCHF₂ OCH₃ F Cl SCHF₂ OCH₃ FSCHF₂ C₂F₅ OCH₃ F Cl C₂F₅ OCH₃ F SCHF₂ Cl OCH₃ F Cl Cl OCH₃ F SCHF₂SCH₂CH₃ OCH₃ F Cl SCH₂CH₃ CH₂CH₃ F CF₃ CF₃ CH₂CH₃ F OCF₃ CF₃ CH₂CH₃ FCF₃ OCF₃ CH₂CH₃ F OCF₃ OCF₃ CH₂CH₃ F CF₃ SCF₃ CH₂CH₃ F OCF₃ SCF₃ CH₂CH₃F CF₃ OCHF₂ CH₂CH₃ F OCF₃ OCHF₂ CH₂CH₃ F CF₃ SCHF₂ CH₂CH₃ F OCF₃ SCHF₂CH₂CH₃ F CF₃ C₂F₅ CH₂CH₃ F OCF₃ C₂F₅ CH₂CH₃ F CF₃ Cl CH₂CH₃ F OCF₃ ClCH₂CH₃ F CF₃ SCH₂CH₃ CH₂CH₃ F OCF₃ SCH₂CH₃ CH₂CH₃ F OCHF₂ CF₃ CH₂CH₃ FSCF₃ CF₃ CH₂CH₃ F OCHF₂ OCF₃ CH₂CH₃ F SCF₃ OCF₃ CH₂CH₃ F OCHF₂ SCF₃CH₂CH₃ F SCF₃ SCF₃ CH₂CH₃ F OCHF₂ OCHF₂ CH₂CH₃ F SCF₃ OCHF₂ CH₂CH₃ FOCHF₂ SCHF₂ CH₂CH₃ F SCF₃ SCHF₂ CH₂CH₃ F OCHF₂ C₂F₅ CH₂CH₃ F SCF₃ C₂F₅CH₂CH₃ F OCHF₂ Cl CH₂CH₃ F SCF₃ Cl CH₂CH₃ F OCHF₂ SCH₂CH₃ CH₂CH₃ F SCF₃SCH₂CH₃ CH₂CH₃ F SCHF₂ CF₃ CH₂CH₃ F Cl CF₃ CH₂CH₃ F SCHF₂ OCF₃ CH₂CH₃ FCl OCF₃ CH₂CH₃ F SCHF₂ SCF₃ CH₂CH₃ F Cl SCF₃ CH₂CH₃ F SCHF₂ OCHF₂ CH₂CH₃F Cl OCHF₂ CH₂CH₃ F SCHF₂ SCHF₂ CH₂CH₃ F Cl SCHF₂ CH₂CH₃ F SCHF₂ C₂F₅CH₂CH₃ F Cl C₂F₅ CH₂CH₃ F SCHF₂ Cl CH₂CH₃ F Cl Cl CH₂CH₃ F SCHF₂ SCH₂CH₃CH₂CH₃ F Cl SCH₂CH₃

TABLE 2

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ CCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ Y is CH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CHOCF₃ OCF₃

TABLE 3

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ OCF₃

TABLE 4

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CR3 CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 5

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 6

R¹ R⁹ R¹ R⁹ R¹ R⁹ R¹ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃CH₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Yare N; Z is CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X is CH; Y and Zare N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ Y is CH; X and Z are NCH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CH₃CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃

TABLE 7

R¹ R⁷ R⁹ Y¹ Z¹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CHCH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N NCH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ NN CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X is N; Y andZ are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N NCH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Y are CH; Z is NCH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH NCH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CHCH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N

TABLE 8

R¹ R⁷ R⁹ X¹ Y¹ Z¹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH CH N CH₂CH₃ CF₃CF₃ CH N CH CH₂CH₃ CF₃ CF₃ N CH CH CH₂CH₃ CF₃ CF₃ CH N N CH₂CH₃ CF₃ OCF₃CH CH N CH₂CH₃ CF₃ OCF₃ CH N CH CH₂CH₃ CF₃ OCF₃ N CH CH CH₂CH₃ CF₃ OCF₃CH N N CH₂CH₃ OCF₃ CF₃ CH CH N CH₂CH₃ OCF₃ CF₃ CH N CH CH₂CH₃ OCF₃ CF₃ NCH CH CH₂CH₃ OCF₃ CF₃ CH N N CH₂CH₃ OCF₃ OCF₃ CH CH N CH₂CH₃ OCF₃ OCF₃CH N CH CH₂CH₃ OCF₃ OCF₃ N CH CH CH₂CH₃ OCF₃ OCF₃ CH N N CH₃ CF₃ CF₃ CHCH N CH₃ CF₃ CF₃ CH N CH CH₃ CF₃ CF₃ CH N N CH₃ CF₃ OCF₃ CH CH N CH₃ CF₃OCF₃ CH N CH CH₃ CF₃ OCF₃ N CH CH CH₃ CF₃ OCF₃ CH N N CH₃ OCF₃ CF₃ CH CHN CH₃ OCF₃ CF₃ CH N CH CH₃ OCF₃ CF₃ N CH CH CH₃ OCF₃ CF₃ CH N N CH₃ OCF₃OCF₃ CH CH N CH₃ OCF₃ OCF₃ CH N CH CH₃ OCF₃ OCF₃ N CH CH CH₃ OCF₃ OCF₃CH N N X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH CH N CH₂CH₃ CF₃ CF₃ CH NCH CH₂CH₃ CF₃ CF₃ N CH CH CH₂CH₃ CF₃ CF₃ CH N N CH₂CH₃ CF₃ OCF₃ CH CH NCH₂CH₃ CF₃ OCF₃ CH N CH CH₂CH₃ CF₃ OCF₃ N CH CH CH₂CH₃ CF₃ OCF₃ CH N NCH₂CH₃ OCF₃ CF₃ CH CH N CH₂CH₃ OCF₃ CF₃ CH N CH CH₂CH₃ OCF₃ CF₃ N CH CHCH₂CH₃ OCF₃ CF₃ CH N N CH₂CH₃ OCF₃ OCF₃ CH CH N CH₂CH₃ OCF₃ OCF₃ CH N CHCH₂CH₃ OCF₃ OCF₃ N CH CH CH₂CH₃ OCF₃ OCF₃ CH N N CH₃ CF₃ CF₃ CH CH N CH₃CF₃ CF₃ CH N CH CH₃ CF₃ CF₃ N CH CH CH₃ CF₃ CF₃ CH N N CH₃ CF₃ OCF₃ CHCH N CH₃ CF₃ OCF₃ CH N CH CH₃ CF₃ OCF₃ N CH CH CH₃ CF₃ OCF₃ CH N N CH₃OCF₃ CF₃ CH CH N CH₃ OCF₃ CF₃ CH N CH CH₃ OCF₃ CF₃ N CH CH CH₃ OCF₃ CF₃CH N N CH₃ OCF₃ OCF₃ CH CH N CH₃ OCF₃ OCF₃ CH N CH CH₃ OCF₃ OCF₃ N CH CHCH₃ OCF₃ OCF₃ CH N N X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH CH NCH₂CH₃ CF₃ CF₃ CH N CH CH₂CH₃ CF₃ CF₃ N CH CH CH₂CH₃ CF₃ CF₃ CH N NCH₂CH₃ CF₃ OCF₃ CH CH N CH₂CH₃ CF₃ OCF₃ CH N CH CH₂CH₃ CF₃ OCF₃ N CH CHCH₂CH₃ CF₃ OCF₃ CH N N CH₂CH₃ OCF₃ CF₃ CH CH N CH₂CH₃ OCF₃ CF₃ CH N CHCH₂CH₃ OCF₃ CF₃ N CH CH CH₂CH₃ OCF₃ CF₃ CH N N CH₂CH₃ OCF₃ OCF₃ CH CH NCH₂CH₃ OCF₃ OCF₃ CH N CH CH₂CH₃ OCF₃ OCF₃ N CH CH CH₂CH₃ OCF₃ OCF₃ CH NN CH₃ CF₃ CF₃ CH CH N CH₃ CF₃ CF₃ CH N CH CH₃ CF₃ CF₃ N CH CH CH₃ CF₃CF₃ CH N N CH₃ CF₃ OCF₃ CH CH N CH₃ CF₃ OCF₃ CH N CH CH₃ CF₃ OCF₃ N CHCH CH₃ CF₃ OCF₃ CH N N CH₃ OCF₃ CF₃ CH CH N CH₃ OCF₃ CF₃ CH N CH CH₃OCF₃ CF₃ N CH CH CH₃ OCF₃ CF₃ CR N N CH₃ OCF₃ OCF₃ CR CH N CH₃ OCF₃ OCF₃CH N CH CH₃ OCF₃ OCF₃ N CH CH CH₃ OCF₃ OCF₃ CH N N

TABLE 9

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 10

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 11

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ CCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ CCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 12

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ CCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ CCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 13

R¹ R⁹ R¹ R⁹ R¹ R⁹ R¹ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃CH₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃X and Z are CH; Y is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Yare CH; Z is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Y are N; Zis CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X is CH; Y and Z are NCH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ Y is CH; X and Z are N CH₂CH₃CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CH₃ CF₃CH₂CH₃ OCF₃ CH₃ OCF₃

TABLE 14

R¹ R⁷ R⁹ Y¹ Z¹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ NN CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Zare CH; Y is N CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ NN CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Y are CH; Z is NCH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH NCH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃OCF₃ OCF₃ N CH CH₂CH₃ CCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CHCH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ NCH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CHCH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N NCH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH NCH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CHCH₃ OCF₃ OCF₃ N N

TABLE 15

R¹ R⁷ R⁹ X¹ Y¹ Z¹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH CH N CH₂CH₃CF₃ CF₃ CH N CH CH₂CH₃ CF₃ CF₃ N CH CH CH₂CH₃ CF₃ CF₃ CH N N CH₂CH₃ CF₃OCF₃ CH CH N CH₂CH₃ CF₃ OCF₃ CH N CH CH₂CH₃ CF₃ OCF₃ N CH CH CH₂CH₃ CF₃OCF₃ CH N N CH₂CH₃ OCF₃ CF₃ CH CH N CH₂CH₃ OCF₃ CF₃ CH N CH CH₂CH₃ OCF₃CF₃ N CH CH CH₂CH₃ OCF₃ CF₃ CH N N CH₂CH₃ OCF₃ OCF₃ CH CH N CH₂CH₃ OCF₃OCF₃ CH N CH CH₂CH₃ OCF₃ OCF₃ N CH CH CH₂CH₃ OCF₃ OCF₃ CH N N CH₃ CF₃CF₃ CH CH N CH₃ CF₃ CF₃ CH N CH CH₃ CF₃ CF₃ N CH CH CH₃ CF₃ CF₃ CH N NCH₃ CF₃ OCF₃ CH CH N CH₃ CF₃ OCF₃ CH N CH CH₃ CF₃ OCF₃ N CH CH CH₃ CF₃OCF₃ CH N N CH₃ OCF₃ CF₃ CH CH N CH₃ OCF₃ CF₃ CH N CH CH₃ OCF₃ CF₃ N CHCH CH₃ OCF₃ CF₃ CH N N CH₃ OCF₃ OCF₃ CH CH N CH₃ OCF₃ OCF₃ CH N CH CH₃OCF₃ OCF₃ N CH CH CH₃ OCF₃ OCF₃ CH N N X and Z are CH; Y is N CH₂CH₃ CF₃CF₃ CH CH N CH₂CH₃ CF₃ CF₃ CH N CH CH₂CH₃ CF₃ CF₃ N CH CH CH₂CH₃ CF₃ CF₃CH N N CH₂CH₃ CF₃ OCF₃ CH CH N CH₂CH₃ CF₃ OCF₃ CH N CH CH₂CH₃ CF₃ OCF₃ NCH CH CH₂CH₃ CF₃ OCF₃ CH N N CH₂CH₃ OCF₃ CF₃ CH CH N CH₂CH₃ OCF₃ CF₃ CHN CH CH₂CH₃ OCF₃ CF₃ N CH CH CH₂CH₃ OCF₃ CF₃ CH N N CH₂CH₃ OCF₃ OCF₃ CHCH N CH₂CH₃ OCF₃ OCF₃ CH N CH CH₂CH₃ OCF₃ OCF₃ N CH CH CH₂CH₃ OCF₃ OCF₃CH N N CH₃ CF₃ CF₃ CH CH N CH₃ CF₃ CF₃ CH N CH CH₃ CF₃ CF₃ N CH CH CH₃CF₃ CF₃ CH N N CH₃ CF₃ OCF₃ CH CH N CH₃ CF₃ OCF₃ CH N CH CH₃ CF₃ OCF₃ NCH CH CH₃ CF₃ OCF₃ CH N N CH₃ OCF₃ CF₃ CH CH N CH₃ OCF₃ CF₃ CH N CH CH₃OCF₃ CF₃ N CH CH CH₃ OCF₃ CF₃ CH N N CH₃ OCF₃ OCF₃ CH CH N CH₃ OCF₃ OCF₃CH N CH CH₃ OCF₃ OCF₃ N CH CH CH₃ OCF₃ OCF₃ CH N N X and Y are CH; Z isN CH₂CH₃ CF₃ CF₃ CH CH N CH₂CH₃ CF₃ CF₃ CH N CH CH₂CH₃ CF₃ CF₃ N CH CHCH₂CH₃ CF₃ CF₃ CH N N CH₂CH₃ CF₃ OCF₃ CH CH N CH₂CH₃ CF₃ OCF₃ CH N CHCH₂CH₃ CF₃ OCF₃ N CH CH CH₂CH₃ CF₃ OCF₃ CH N N CH₂CH₃ OCF₃ CF₃ CH CH NCH₂CH₃ OCF₃ CF₃ CH N CH CH₂CH₃ OCF₃ CF₃ N CH CH CH₂CH₃ OCF₃ CF₃ CH N NCH₂CH₃ OCF₃ OCF₃ CH CH N CH₂CH₃ OCF₃ OCF₃ CH N CH CH₂CH₃ OCF₃ OCF₃ N CHCH CH₂CH₃ OCF₃ OCF₃ CH N N CH₃ CF₃ CF₃ CH CH N CH₃ CF₃ CF₃ CH N CH CH₃CF₃ CF₃ N CH CH CH₃ CF₃ CF₃ CH N N CH₃ CF₃ OCF₃ CH CH N CH₃ CF₃ OCF₃ CHN CH CH₃ CF₃ OCF₃ N CH CH CH₃ CF₃ OCF₃ CR N N CH₃ OCF₃ CF₃ CH CH N CH₃OCF₃ CF₃ CH N CH CH₃ OCF₃ CF₃ N CH CH CH₃ OCF₃ CF₃ CH N N CH₃ OCF₃ OCF₃CH CH N CH₃ OCF₃ OCF₃ CH N CH CH₃ OCF₃ OCF₃ N CH CH CH OCF₃ OCF₃ CH N N

TABLE 16

R³ is H; X, Y and Z are CH R¹ R⁴ R⁵ R⁹ R¹ R⁴ R⁵ R⁹ CH₂CH₃ H CF₃ CF₃CH₂CH₃ H OCF₃ CF₃ CH₂CH₃ H CF₃ OCF₃ CH₂CH₃ H OCF₃ OCF₃ CH₂CH₃ H CF₃ SCF₃CH₂CH₃ H OCF₃ SCF₃ CH₂CH₃ H CF₃ OCHF₂ CH₂CH₃ H OCF₃ OCHF₂ CH₂CH₃ H CF₃SCHF₂ CH₂CH₃ H OCF₃ SCHF₂ CH₂CH₃ H CF₃ C₂F₅ CH₂CH₃ H OCF₃ C₂F₅ CH₂CH₃ HCF₃ Cl CH₂CH₃ H OCF₃ Cl CH₂CH₃ H CF₃ SCH₂CH₃ CH₂CH₃ H OCF₃ SCH₂CH₃CH₂CH₃ H OCHF₂ CF₃ CH₂CH₃ H SCF₃ CF₃ CH₂CH₃ H OCHF₂ OCF₃ CH₂CH₃ H SCF₃OCF₃ CH₂CH₃ H OCHF₂ SCF₃ CH₂CH₃ H SCF₃ SCF₃ CH₂CH₃ H OCHF₂ OCHF₂ CH₂CH₃H SCF₃ OCHF₂ CH₂CH₃ H OCHF₂ SCHF₂ CH₂CH₃ H SCF₃ SCHF₂ CH₂CH₃ H OCHF₂C₂F₅ CH2CH₃ H SCF₃ C₂F₅ CH₂CH₃ H OCHF₂ Cl CH₂CH₃ H SCF₃ Cl CH₂CH₃ HOCHF₂ SCH₂CH₃ CH₂CH₃ H SCF₃ SCH₂CH₃ CH₂CH₃ H SCHF₂ CF₃ CH₂CH₃ H Cl CF₃CH₂CH₃ H SCHF₂ OCF₃ CH₂CH₃ H Cl OCF₃ CH₂CH₃ H SCHF₂ SCF₃ CH₂CH₃ H ClSCF₃ CH₂CH₃ H SCHF₂ OCHF₂ CH₂CH₃ H Cl OCHF₂ CH₂CH₃ H SCHF₂ SCHF₂ CH₂CH₃H Cl SCHF₂ CH₂CH₃ H SCHF₂ C₂F₅ CH₂CH₃ H Cl C₂F₅ CH₂CH₃ H SCHF₂ Cl CH₂CH₃H Cl Cl CH₂CH₃ H SCHF₂ SCH₂CH₃ CH₂CH₃ H Cl SCH₂CH₃ CH₂CH₃ CH₃ CF₃ CF₃CH₂CH₃ CH₃ OCF₃ CF₃ CH₂CH₃ CH₃ CF₃ OCF₃ CH₂CH₃ CH₃ OCF₃ OCF₃ CH₂CH₃ CH₃CF₃ SCF₃ CH₂CH₃ CH₃ OCF₃ SCF₃ CH₂CH₃ CH₃ CF₃ OCHF₂ CH₂CH₃ CH₃ OCF₃ OCHF₂CH₂CH₃ CH₃ CF₃ SCHF₂ CH₂CH₃ CH₃ OCF₃ SCHF₂ CH₂CH₃ CH₃ CF₃ C₂F₅ CH₂CH₃CH₃ OCF₃ C₂F₅ CH₂CH₃ CH₃ CF₃ Cl CH₂CH₃ CH₃ OCF₃ Cl CH₂CH₃ CH₃ CF₃SCH₂CH₃ CH₂CH₃ CH₃ OCF₃ SCH₂CH₃ CH₂CH₃ CH₃ OCHF₂ CF₃ CH₂CH₃ CH₃ SCF₃ CF₃CH₂CH₃ CH₃ OCHF₂ OCF₃ CH₂CH₃ CH₃ SCF₃ OCF₃ CH₂CH₃ CH₃ OCHF₂ SCF₃ CH₂CH₃CH₃ SCF₃ SCF₃ CH₂CH₃ CH₃ OCHF₂ OCHF₂ CH₂CH₃ CH₃ SCF₃ OCHF₂ CH₂CH₃ CH₃OCHF₂ SCHF₂ CH₂CH₃ CH₃ SCF₃ SCHF₂ CH₂CH₃ CH₃ OCHF₂ C₂F₅ CH₂CH₃ CH₃ SCF₃C₂F₅ CH₂CH₃ CH₃ OCHF₂ Cl CH₂CH₃ CH₃ SCF₃ Cl CH₂CH₃ CH₃ OCHF₂ SCH₂CH₃CH₂CH₃ CH₃ SCF₃ SCH₂CH₃ CH₂CH₃ CH₃ SCHF₂ CF₃ CH₂CH₃ CH₃ Cl CF₃ CH₂CH₃CH₃ SCHF₂ OCF₃ CH₂CH₃ CH₃ Cl OCF₃ CH₂CH₃ CH₃ SCHF₂ SCF₃ CH₂CH₃ CH₃ ClSCF₃ CH₂CH₃ CH₃ SCHF₂ OCHF₂ CH₂CH₃ CH₃ Cl OCHF₂ CH₂CH₃ CH₃ SCHF₂ SCHF₂CH₂CH₃ CH₃ Cl SCHF₂ CH₂CH₃ CH₃ SCHF₂ C₂F₅ CH₂CH₃ CH₃ Cl C₂F₅ CH₂CH₃ CH₃SCHF₂ Cl CH₂CH₃ CH₃ Cl Cl CH₂CH₃ CH₃ SCHF₂ SCH₂CH₃ CH₂CH₃ CH₃ Cl SCH₂CH₃CH₂CH₃ F CF₃ CF₃ CH₂CH₃ F OCF₃ CF₃ CH₂CH₃ F CF₃ OCF₃ CH₂CH₃ F OCF₃ OCF₃CH₂CH₃ F CF₃ SCF₃ CH₂CH₃ F OCF₃ SCF₃ CH₂CH₃ F CF₃ OCHF₂ CH₂CH₃ F OCF₃OCHF₂ CH₂CH₃ F CF₃ SCHF₂ CH₂CH₃ F OCF₃ SCHF₂ CH₂CH₃ F CF₃ C₂F₅ CH₂CH₃ FOCF₃ C₂F₅ CH₂CH₃ F CF₃ Cl CH₂CH₃ F OCF₃ Cl CH₂CH₃ F CF₃ SCH₂CH₃ CH₂CH₃ FOCF₃ SCH₂CH₃ CH₂CH₃ F OCHF₂ CF₃ CH₂CH₃ F SCF₃ CF₃ CH₂CH₃ F OCHF₂ OCF₃CH₂CH₃ F SCF₃ OCF₃ CH₂CH₃ F OCHF₂ SCF₃ CH₂CH₃ F SCF₃ SCF₃ CH₂CH₃ F OCHF₂OCHF₂ CH₂CH₃ F SCF₃ OCHF₂ CH₂CH₃ F OCHF₂ SCHF₂ CH₂CH₃ F SCF₃ SCHF₂CH₂CH₃ F OCHF₂ C₂F₅ CH₂CH₃ F SCF₃ C₂F₅ CH₂CH₃ F OCHF₂ Cl CH₂CH₃ F SCF₃Cl CH₂CH₃ F OCHF₂ SCH₂CH₃ CH₂CH₃ F SCF₃ SCH₂CH₃ CH₂CH₃ F SCHF₂ CF₃CH₂CH₃ F Cl CF₃ CH₂CH₃ F SCHF₂ OCF₃ CH₂CH₃ F Cl OCF₃ CH₂CH₃ F SCHF₂ SCF₃CH₂CH₃ F Cl SCF₃ CH₂CH₃ F SCHF₂ OCHF₂ CH₂CH₃ F Cl OCHF₂ CH₂CH₃ F SCHF₂SCHF₂ CH₂CH₃ F Cl SCHF₂ CH₂CH₃ F SCHF₂ C₂F₅ CH₂CH₃ F Cl C₂F₅ CH₂CH₃ FSCHF₂ Cl CH₂CH₃ F Cl Cl CH₂CH₃ F SCHF₂ SCH₂CH₃ CH₂CH₃ F Cl SCH₂CH₃CH₂CH₃ Cl CF₃ CF₃ CH₂CH₃ Cl OCF₃ CF₃ CH₂CH₃ Cl CF₃ OCF₃ CH₂CH₃ Cl OCF₃OCF₃ CH₂CH₃ Cl CF₃ SCF₃ CH₂CH₃ Cl OCF₃ SCF₃ CH₂CH₃ Cl CF₃ ClCHF2 CH₂CH₃Cl OCF₃ OCHF₂ CH₂CH₃ Cl CF₃ SCHF₂ CH₂CH₃ Cl OCF₃ SCHF₂ CH₂CH₃ Cl CF₃C₂F₅ CH₂CH₃ Cl OCF₃ C₂F₅ CH₂CH₃ Cl CF₃ Cl CH₂CH₃ Cl OCF₃ Cl CH₂CH₃ ClCF₃ SCH₂CH₃ CH₂CH₃ Cl OCF₃ SCH₂CH₃ CH₂CH₃ Cl OCHF₂ CF₃ CH₂CH₃ Cl SCF₃CF₃ CH₂CH₃ Cl OCHF₂ OCF₃ CH₂CH₃ Cl SCF₃ OCF₃ CH₂CH₃ Cl OCHF₂ SCF₃ CH₂CH₃Cl SCF₃ SCF₃ CH₂CH₃ Cl OCHF₂ OCHF₂ CH₂CH₃ Cl SCF₃ OCHF₂ CH₂CH₃ Cl OCHF₂SCHF₂ CH₂CH₃ Cl SCF₃ SCHF₂ CH₂CH₃ Cl OCHF₂ C₂F₅ CH₂CH₃ Cl SCF₃ C₂F₅CH₂CH₃ Cl OCHF₂ Cl CH₂CH₃ Cl SCF₃ Cl CH₂CH₃ Cl OCHF₂ SCH₂CH₃ CH₂CH₃ ClSCF₃ SCH₂CH₃ CH₂CH₃ Cl SCHF₂ CF₃ CH₂CH₃ Cl Cl CF₃ CH₂CH₃ Cl SCHF₂ OCF₃CH₂CH₃ Cl Cl OCF₃ CH₂CH₃ Cl SCHF₂ SCF₃ CH₂CH₃ Cl Cl SCF₃ CH₂CH₃ Cl SCHF₂OCHF₂ CH₂CH₃ Cl Cl OCHF₂ CH₂CH₃ Cl SCHF₂ SCHF₂ CH₂CH₃ Cl Cl SCHF₂ CH₂CH₃Cl SCHF₂ C₂F₅ CH₂CH₃ Cl Cl C₂F₅ CH₂CH₃ Cl SCHF₂ Cl CH₂CH₃ Cl Cl ClCH₂CH₃ Cl SCHF₂ SCH₂CH₃ CH₂CH₃ Cl Cl SCH₂CH₃ CH₃ H CF₃ CF₃ CH₃ H OCF₃CF₃ CH₃ H CF₃ OCF₃ CH₃ H OCF₃ OCF₃ CH₃ H CF₃ SCF₃ CH₃ H OCF₃ SCF₃ CH₃ HCF₃ OCHF₂ CH₃ H OCF₃ OCHF₂ CH₃ H CF₃ SCHF₂ CH₃ H OCF₃ SCHF₂ CH₃ H CF₃C₂F₅ CH₃ H OCF₃ C₂F₅ CH₃ H CF₃ Cl CH₃ H OCF₃ Cl CH₃ H CF₃ SCH₂CH₃ CH₃ HOCF₃ SCH₂CH₃ CH₃ H OCHF₂ CF₃ CH₃ H SCF₃ CF₃ CH₃ H OCHF₂ OCF₃ CH₃ H SCF₃OCF₃ CH₃ H OCHF₂ SCF₃ CH₃ H SCF₃ SCF₃ CH₃ H OCHF₂ OCHF₂ CH₃ H SCF₃ OCHF₂CH₃ H OCHF₂ SCHF₂ CH₃ H SCF₃ SCHF₂ CH₃ H OCHF₂ C₂F₅ CH₃ H SCF₃ C₂F₅ CH₃H OCHF₂ Cl CH₃ H SCF₃ Cl CH₃ H OCHF₂ SCH₂CH₃ CH₃ H SCF₃ SCH₂CH₃ CH₃ HSCHF₂ CF₃ CH₃ H Cl CF₃ CH₃ H SCHF₂ OCF₃ CH₃ H Cl OCF₃ CH₃ H SCHF₂ SCF₃CH₃ H Cl SCF₃ CH₃ H SCHF₂ OCHF₂ CH₃ H Cl OCHF₂ CH₃ H SCHF₂ SCHF₂ CH₃ HCl SCHF₂ CH₃ H SCHF₂ C₂F₅ CH₃ H Cl C₂F₅ CH₃ H SCHF₂ Cl CH₃ H Cl CH₃ HSCHF₂ SCH₂CH₃ CH₃ H Cl SCH₂CH₃ CH₃ CH₃ CF₃ CF₃ CH₃ CH₃ OCF₃ CF₃ CH₃ CH₃CF₃ OCF₃ CH₃ CH₃ OCF₃ OCF₃ CH₃ CH₃ CF₃ SCF₃ CH₃ CH₃ OCF₃ SCF₃ CH₃ CH₃CF₃ OCHF₂ CH₃ CH₃ OCF₃ OCHF₂ CH₃ CH₃ CF₃ SCHF₂ CH₃ CH₃ OCF₃ SCHF₂ CH₃CH₃ CF₃ C₂F₅ CH₃ CH₃ OCF₃ C₂F₅ CH₃ CH₃ CF₃ Cl CH₃ CH₃ OCF₃ Cl CH₃ CH₃CF₃ SCH₂CH₃ CH₃ CH₃ OCF₃ SCH₂CH₃ CH₃ CH₃ OCHF₂ CF₃ CH₃ CH₃ SCF₃ CF₃ CH₃CH₃ OCHF₂ OCF₃ CH₃ CH₃ SCF₃ OCF₃ CH₃ CH₃ OCHF₂ SCF₃ CH₃ CH₃ SCF₃ SCF₃CH₃ CH₃ OCHF₂ OCHF₂ CH₃ CH₃ SCF₃ OCHF₂ CH₃ CH₃ OCHF₂ SCHF₂ CH₃ CH₃ SCF₃SCHF₂ CH₃ CH₃ OCHF₂ C₂F₅ CH₃ CH₃ SCF₃ C₂F₅ CH₃ CH₃ OCHF₂ Cl CH₃ CH₃ SCF₃Cl CH₃ CH₃ OCHF₂ SCH₂CH₃ CH₃ CH₃ SCF₃ SCH₂CH₃ CH₃ CH₃ SCHF₂ CF₃ CH₃ CH₃Cl CF₃ CH₃ CH₃ SCHF₂ OCF₃ CH₃ CH₃ Cl OCF₃ CH₃ CH₃ SCHF₂ SCF₃ CH₃ CH₃ ClSCF₃ CH₃ CH₃ SCHF₂ OCHF₂ CH₃ CH₃ Cl OCHF₂ CH₃ CH₃ SCHF₂ SCHF₂ CH₃ CH₃ ClSCHF₂ CH₃ CH₃ SCHF₂ C₂F₅ CH₃ CH₃ Cl C₂F₅ CH₃ CH₃ SCHF₂ Cl CH₃ CH₃ Cl CH₃CH₃ SCHF₂ SCH₂CH₃ CH₃ CH₃ Cl SCH₂CH₃ CH₃ F CF₃ CF₃ CH₃ F OCF₃ CF₃ CH₃ FCF₃ OCF₃ CH₃ F OCF₃ OCF₃ CH₃ F CF₃ SCF₃ CH₃ F OCF₃ SCF₃ CH₃ F CF₃ OCHF₂CH₃ F OCF₃ OCHF₂ CH₃ F CF₃ SCHF₂ CH₃ F OCF₃ SCHF₂ CH₃ F CF₃ C₂F₅ CH₃ FOCF₃ C₂F₅ CH₃ F CF₃ Cl CH₃ F OCF₃ Cl CH₃ F CF₃ SCH₂CH₃ CH₃ F OCF₃SCH₂CH₃ CH₃ F OCHF₂ CF₃ CH₃ F SCF₃ CF₃ CH₃ F OCHF₂ OCF₃ CH₃ F SCF₃ OCF₃CH₃ F OCHF₂ SCF₃ CH₃ F SCF₃ SCF₃ CH₃ F OCHF₂ OCHF₂ CH₃ F SCF₃ OCHF₂ CH₃F OCHF₂ SCHF₂ CH₃ F SCF₃ SCHF₂ CH₃ F OCHF₂ C₂F₅ CH₃ F SCF₃ C₂F₅ CH₃ FOCHF₂ Cl CH₃ F SCF₃ Cl CH₃ F OCHF₂ SCH₂CH₃ CH₃ F SCF₃ SCH₂CH₃ CH₃ FSCHF₂ CF₃ CH₃ F Cl CF₃ CH₃ F SCHF₂ OCF₃ CH₃ F Cl OCF₃ CH₃ F SCHF₂ SCF₃CH₃ F Cl SCF₃ CH₃ F SCHF₂ OCHF₂ CH₃ F Cl OCHF₂ CH₃ F SCHF₂ SCHF₂ CH₃ FCl SCHF₂ CH₃ F SCHF₂ C₂F₅ CH₃ F Cl C₂F₅ CH₃ F SCHF₂ Cl CH₃ F Cl Cl CH₃ FSCHF₂ SCH₂CH₃ CH₃ F Cl SCH₂CH₃ CH₃ Cl CF₃ CF₃ CH₃ Cl OCF₃ CF₃ CH₃ Cl CF₃OCF₃ CH₃ Cl OCF₃ OCF₃ CH₃ Cl CF₃ SCF₃ CH₃ Cl OCF₃ SCF₃ CH₃ Cl CF₃ OCHF₂CH₃ Cl OCF₃ OCHF₂ CH₃ Cl CF₃ SCHF₂ CH₃ Cl OCF₃ SCHF₂ CH₃ Cl CF₃ C₂F₅ CH₃Cl OCF₃ C₂F₅ CH₃ Cl CF₃ Cl CH₃ Cl OCF₃ Cl CH₃ Cl CF₃ SCH₂CH₃ CH₃ Cl OCF₃SCH₂CH₃ CH₃ Cl OCHF₂ CF₃ CH₃ Cl SCF₃ CF₃ CH₃ Cl OCHF₂ OCF₃ CH₃ Cl SCF₃OCF₃ CH₃ Cl OCHF₂ SCF₃ CH₃ Cl SCF₃ SCF₃ CH₃ Cl OCHF₂ OCHF₂ CH₃ Cl SCF₃OCHF₂ CH₃ Cl OCHF₂ SCHF₂ CH₃ Cl SCF₃ SCHF₂ CH₃ Cl OCHF₂ C₂F₅ CH₃ Cl SCF₃C₂F₅ CH₃ Cl OCHF₂ Cl CH₃ Cl SCF₃ Cl CH₃ Cl OCHF₂ SCH₂CH₃ CH₃ Cl SCF₃SCH₂CH₃ CH₃ Cl SCHF₂ CF₃ CH₃ Cl Cl CF₃ CH₃ Cl SCHF₂ OCF₃ CH₃ Cl Cl OCF₃CH₃ Cl SCHF₂ SCF₃ CH₃ Cl Cl SCF₃ CH₃ Cl SCHF₂ OCHF₂ CH₃ Cl Cl OCHF₂ CH₃Cl SCHF₂ SCHF₂ CH₃ Cl Cl SCHF₂ CH₃ Cl SCHF₂ C₂F₅ CH₃ Cl Cl C₂F₅ CH₃ ClSCHF₂ Cl CH₃ Cl Cl Cl CH₃ Cl SCHF₂ SCH₂CH₃ CH₃ Cl Cl SCH₂CH₃

TABLE 17

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ Y is CH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃

TABLE 18

X, Y and Z are CH R¹ R⁵ R⁹ R¹ R⁵ R⁹ H CF₃ CF₃ H OCF₃ CF₃ H CF₃ OCF₃ HOCF₃ OCF₃ H CF₃ SCF₃ H OCF₃ SCF₃ H CF₃ OCHF₂ H OCF₃ OCHF₂ H CF₃ SCHF₂ HOCF₃ SCHF₂ H CF₃ C₂F₅ H OCF₃ C₂F₅ H CF₃ Cl H OCF₃ Cl H CF₃ SCH₂CH₃ HOCF₃ SCH₂CH₃ H OCHF₂ CF₃ H SCF₃ CF₃ H OCHF₂ OCF₃ H SCF₃ OCF₃ H OCHF₂SCF₃ H SCF₃ SCF₃ H OCHF₂ OCHF₂ H SCF₃ OCHF₂ H OCHF₂ SCHF₂ H SCF₃ SCHF₂ HOCHF₂ C₂F₅ H SCF₃ C₂F₅ H OCHF₂ Cl H SCF₃ Cl H OCHF₂ SCH₂CH₃ H SCF₃SCH₂CH₃ H SCHF₂ CF₃ H Cl CF₃ H SCHF₂ OCF₃ H Cl OCF₃ H SCHF₂ SCF₃ H ClSCF₃ H SCHF₂ OCHF₂ H Cl OCHF₂ H SCHF₂ SCHF₂ H Cl SCHF₂ H SCHF₂ C₂F₅ H ClC₂F₅ H SCHF₂ Cl H Cl Cl H SCHF₂ SCH₂CH₃ H Cl SCH₂CH₃ CH₃ CF₃ CF₃ CH₃OCF₃ CF₃ CH₃ CF₃ OCF₃ CH₃ OCF₃ OCF₃ CH₃ CF₃ SCF₃ CH₃ OCF₃ SCF₃ CH₃ CF₃OCHF₂ CH₃ OCF₃ OCHF₂ CH₃ CF₃ SCHF₂ CH₃ OCF₃ SCHF₂ CH₃ CF₃ C₂F₅ CH₃ OCF₃C₂F₅ CH₃ CF₃ Cl CH₃ OCF₃ Cl CH₃ CF₃ SCH₂CH₃ CH₃ OCF₃ SCH₂CH₃ CH₃ OCHF₂CF₃ CH₃ SCF₃ CF₃ CH₃ OCHF₂ OCF₃ CH₃ SCF₃ OCF₃ CH₃ OCHF₂ SCF₃ CH₃ SCF₃SCF₃ CH₃ OCHF₂ OCHF₂ CH₃ SCF₃ OCHF₂ CH₃ OCHF₂ SCHF₂ CH₃ SCF₃ SCHF₂ CH₃OCHF₂ C₂F₅ CH₃ SCF₃ C₂F₅ CH₃ OCHF₂ Cl CH₃ SCF₃ Cl CH₃ OCHF₂ SCH₂CH₃ CH₃SCF₃ SCH₂CH₃ CH₃ SCHF₂ CF₃ CH₃ Cl CF₃ CH₃ SCHF₂ OCF₃ CH₃ Cl OCF₃ CH₃SCHF₂ SCF₃ CH₃ Cl SCF₃ CH₃ SCHF₂ OCHF₂ CH₃ Cl OCHF₂ CH₃ SCHF₂ SCHF₂ CH₃Cl SCHF₂ CH₃ SCHF₂ C₂F₅ CH₃ Cl C₂F₅ CH₃ SCHF₂ Cl CH₃ Cl Cl CH₃ SCHF₂SCH₂CH₃ CH₃ Cl SCH₂CH₃ OCH₃ CF₃ CF₃ OCH₃ OCF₃ CF₃ OCH₃ CF₃ OCF₃ OCH₃OCF₃ OCF₃ OCH₃ CF₃ SCF₃ OCH₃ OCF₃ SCF₃ OCH₃ CF₃ OCHF₂ OCH₃ OCF₃ OCHF₂OCH₃ CF₃ SCHF₂ OCH₃ OCF₃ SCHF₂ OCH₃ CF₃ C₂F₅ OCH₃ OCF₃ C₂F₅ OCH₃ CF₃ ClOCH₃ OCF₃ Cl OCH₃ CF₃ SCH₂CH₃ OCH₃ OCF₃ SCH₂CH₃ OCH₃ OCHF₂ CF₃ OCH₃ SCF₃CF₃ OCH₃ OCHF₂ OCF₃ OCH₃ SCF₃ OCF₃ OCH₃ OCHF₂ SCF₃ OCH₃ SCF₃ SCF₃ OCH₃OCHF₂ OCHF₂ OCH₃ SCF₃ OCHF₂ OCH₃ OCHF₂ SCHF₂ OCH₃ SCF₃ SCHF₂ OCH₃ OCHF₂C₂F₅ OCH₃ SCF₃ C₂F₅ OCH₃ OCHF₂ Cl OCH₃ SCF₃ Cl OCH₃ OCHF₂ SCH₂CH₃ OCH₃SCF₃ SCH₂CH₃ OCH₃ SCHF₂ CF₃ OCH₃ Cl CF₃ OCH₃ SCHF₂ OCF₃ OCH₃ Cl OCF₃OCH₃ SCHF₂ SCF₃ OCH₃ Cl SCF₃ OCH₃ SCHF₂ OCHF₂ OCH₃ Cl OCHF₂ OCH₃ SCHF₂SCHF₂ OCH₃ Cl SCHF₂ OCH₃ SCHF₂ C₂F₅ OCH₃ Cl C₂F₅ OCH₃ SCHF₂ Cl OCH₃ ClCl OCH₃ SCHF₂ SCH₂CH₃ OCH₃ Cl SCH₂CH₃ CH₂CH₃ CF₃ CF₃ CH₂CH₃ OCF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ OCF₃ CH₂CH₃ CF₃ SCF₃ CH₂CH₃ OCF₃ SCF₃ CH₂CH₃CF₃ OCHF₂ CH₂CH₃ OCF₃ OCHF₂ CH₂CH₃ CF₃ SCHF₂ CH₂CH₃ OCF₃ SCHF₂ CH₂CH₃CF₃ C₂F₅ CH₂CH₃ OCF₃ C₂F₅ CH₂CH₃ CF₃ Cl CH₂CH₃ OCF₃ Cl CH₂CH₃ CF₃SCH₂CH₃ CH₂CH₃ OCF₃ SCH₂CH₃ CH₂CH₃ OCHF₂ CF₃ CH₂CH₃ SCF₃ CF₃ CH₂CH₃OCHF₂ OCF₃ CH₂CH₃ SCF₃ OCF₃ CH₂CH₃ OCHF₂ SCF₃ CH₂CH₃ SCF₃ SCF₃ CH₂CH₃OCHF₂ OCHF₂ CH₂CH₃ SCF₃ OCHF₂ CH₂CH₃ OCHF₂ SCHF₂ CH₂CH₃ SCF₃ SCHF₂CH₂CH₃ OCHF₂ C₂F₅ CH₂CH₃ SCF₃ C₂F₅ CH₂CH₃ OCHF₂ Cl CH₂CH₃ SCF₃ Cl CH₂CH₃OCHF₂ SCH₂CH₃ CH₂CH₃ SCF₃ SCH₂CH₃ CH₂CH₃ SCHF₂ CF₃ CH₂CH₃ Cl CF₃ CH₂CH₃SCHF₂ OCF₃ CH₂CH₃ Cl OCF₃ CH₂CH₃ SCHF₂ SCF₃ CH₂CH₃ Cl SCF₃ CH₂CH₃ SCHF₂OCHF₂ CH₂CH₃ Cl OCHF₂ CH₂CH₃ SCHF₂ SCHF₂ CH₂CH₃ Cl SCHF₂ CH₂CH₃ SCHF₂C₂F₅ CH₂CH₃ Cl C₂F₅ CH₂CH₃ SCHF₂ Cl CH₂CH₃ Cl Cl CH₂CH₃ SCHF₂ SCH₂CH₃CH₂CH₃ Cl SCH₂CH₃

TABLE 19

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ Y is CH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃

TABLE 20

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 21

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 22

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 23

R¹ R⁹ R¹ R⁹ R¹ R⁹ R¹ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃CH₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Yare N; Z is CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X is CH; Y and Zare N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ Y is CH; X and Z are NCH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CH₃CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃

TABLE 24

R¹ R⁷ R⁹ Y¹ Z¹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CHCH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N NCH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ NN CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X is N; Y andZ are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N NCH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Y are CH; Z is NCH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH NCH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CHCH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N

TABLE 25

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ H OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 26

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 27

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 28

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xand Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X isCH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 29

R¹ R⁹ R¹ R⁹ R¹ R⁹ R¹ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃CH₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃X and Z are CH; Y is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Yare CH; Z is N CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X and Y are N; Zis CH CH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X is CH; Y and Z are NCH₂CH₃ CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ Y is CH; X and Z are N CH₂CH₃CF₃ CH₃ CF₃ CH₂CH₃ OCF₃ CH₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CH₃ CF₃CH₂CH₃ OCF₃ CH₃ OCF₃

TABLE 30

R¹ R⁷ R⁹ Y¹ Z¹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ NN CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Zare CH; Y is N CH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ NN CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃CH N CH₂CH₃ OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃CF₃ N CH CH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃OCF₃ N N CH₃ OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃OCF₃ CH N CH₃ OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X and Y are CH; Z is NCH₂CH₃ CF₃ CF₃ CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃OCF₃ CH N CH₂CH₃ CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH NCH₂CH₃ OCF₃ CF₃ N CH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃OCF₃ OCF₃ N CH CH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CHCH₃ CF₃ CF₃ N N CH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃OCF₃ CF₃ CH N CH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃OCF₃ OCF₃ N CH CH₃ OCF₃ OCF₃ N N X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃CH N CH₂CH₃ CF₃ CF₃ N CH CH₂CH₃ CF₃ CF₃ N N CH₂CH₃ CF₃ OCF₃ CH N CH₂CH₃CF₃ OCF₃ N CH CH₂CH₃ CF₃ OCF₃ N N CH₂CH₃ OCF₃ CF₃ CH N CH₂CH₃ OCF₃ CF₃ NCH CH₂CH₃ OCF₃ CF₃ N N CH₂CH₃ OCF₃ OCF₃ CH N CH₂CH₃ OCF₃ OCF₃ N CHCH₂CH₃ OCF₃ OCF₃ N N CH₃ CF₃ CF₃ CH N CH₃ CF₃ CF₃ N CH CH₃ CF₃ CF₃ N NCH₃ CF₃ OCF₃ CH N CH₃ CF₃ OCF₃ N CH CH₃ CF₃ OCF₃ N N CH₃ OCF₃ CF₃ CH NCH₃ OCF₃ CF₃ N CH CH₃ OCF₃ CF₃ N N CH₃ OCF₃ OCF₃ CH N CH₃ OCF₃ OCF₃ N CHCH₃ OCF₃ OCF₃ N N

TABLE 31

X, Y and Z are CH R¹ R⁵ R⁹ R¹ R⁵ R⁹ CH₂CH₃ CF₃ CF₃ CH₂CH₃ OCF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ OCF₃ CH₂CH₃ CF₃ SCF₃ CH₂CH₃ OCF₃ SCF₃ CH₂CH₃CF₃ OCHF₂ CH₂CH₃ OCF₃ OCHF₂ CH₂CH₃ CF₃ SCHF₂ CH₂CH₃ OCF₃ SCHF₂ CH₂CH₃CF₃ C₂F₅ CH₂CH₃ OCF₃ C₂F₅ CH₂CH₃ CF₃ Cl CH₂CH₃ OCF₃ Cl CH₂CH₃ CF₃SCH₂CH₃ CH₂CH₃ OCF₃ SCH₂CH₃ CH₂CH₃ OCHF₂ CF₃ CH₂CH₃ SCF₃ CF₃ CH₂CH₃OCHF₂ OCF₃ CH₂CH₃ SCF₃ OCF₃ CH₂CH₃ OCHF₂ SCF₃ CH₂CH₃ SCF₃ SCF₃ CH₂CH₃OCHF₂ OCHF₂ CH₂CH₃ SCF₃ OCHF₂ CH₂CH₃ OCHF₂ SCHF₂ CH₂CH₃ SCF₃ SCHF₂CH₂CH₃ OCHF₂ C₂F₅ CH₂CH₃ SCF₃ C₂F₅ CH₂CH₃ OCHF₂ Cl CH₂CH₃ SCF₃ Cl CH₂CH₃OCHF₂ SCH₂CH₃ CH₂CH₃ SCF₃ SCH₂CH₃ CH₂CH₃ SCHF₂ CF₃ CH₂CH₃ Cl CF₃ CH₂CH₃SCHF₂ OCF₃ CH₂CH₃ Cl OCF₃ CH₂CH₃ SCHF₂ SCF₃ CH₂CH₃ Cl SCF₃ CH₂CH₃ SCHF₂OCHF₂ CH₂CH₃ Cl OCHF₂ CH₂CH₃ SCHF₂ SCHF₂ CH₂CH₃ Cl SCHF₂ CH₂CH₃ SCHF₂C₂F₅ CH₂CH₃ Cl C₂F₅ CH₂CH₃ SCHF₂ Cl CH₂CH₃ Cl Cl CH₂CH₃ SCHF₂ SCH₂CH₃CH₂CH₃ Cl SCH₂CH₃ CH₃ CF₃ CF₃ CH₃ OCF₃ CF₃ CH₃ CF₃ OCF₃ CH₃ OCF₃ OCF₃CH₃ CF₃ SCF₃ CH₃ OCF₃ SCF₃ CH₃ CF₃ OCHF₂ CH₃ OCF₃ OCHF₂ CH₃ CF₃ SCHF₂CH₃ OCF₃ SCHF₂ CH₃ CF₃ C₂F₅ CH₃ OCF₃ C₂F₅ CH₃ CF₃ Cl CH₃ OCF₃ Cl CH₃ CF₃SCH₂CH₃ CH₃ OCF₃ SCH₂CH₃ CH₃ OCHF₂ CF₃ CH₃ SCF₃ CF₃ CH₃ OCHF₂ OCF₃ CH₃SCF₃ OCF₃ CH₃ OCHF₂ SCF₃ CH₃ SCF₃ SCF₃ CH₃ OCHF₂ OCHF₂ CH₃ SCF₃ OCHF₂CH₃ OCHF₂ SCHF₂ CH₃ SCF₃ SCHF₂ CH₃ OCHF₂ C₂F₅ CH₃ SCF₃ C₂F₅ CH₃ OCHF₂ ClCH₃ SCF₃ Cl CH₃ OCHF₂ SCH₂CH₃ CH₃ SCF₃ SCH₂CH₃ CH₃ SCHF₂ CF₃ CH₃ Cl CF₃CH₃ SCHF₂ OCF₃ CH₃ Cl OCF₃ CH₃ SCHF₂ SCF₃ CH₃ Cl SCF₃ CH₃ SCHF₂ OCHF₂CH₃ Cl OCHF₂ CH₃ SCHF₂ SCHF₂ CH₃ Cl SCHF₂ CH₃ SCHF₂ C₂F₅ CH₃ Cl C₂F₅ CH₃SCHF₂ Cl CH₃ Cl Cl CH₃ SCHF₂ SCH₂CH₃ CH₃ Cl SCH₂CH₃

TABLE 32

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Z are CH; Y is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X is CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ Y is CH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃OCF₃ CH₃ OCF₃ OCF₃ X, Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃

TABLE 33

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

TABLE 34

R¹ R⁵ R⁹ R¹ R⁵ R⁹ X, Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃CF₃ OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃OCF₃ OCF₃ X is N; Y and Z are CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃OCF₃ CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃OCF₃ X and Y are CH; Z is N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃CH₃ CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃X and Y are N; Z is CH CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃CF₃ OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Xis CH; Y and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ Y isCH; X and Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃OCF₃ CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃ X, Yand Z are N CH₂CH₃ CF₃ CF₃ CH₃ CF₃ CF₃ CH₂CH₃ CF₃ OCF₃ CH₃ CF₃ OCF₃CH₂CH₃ OCF₃ CF₃ CH₃ OCF₃ CF₃ CH₂CH₃ OCF₃ OCF₃ CH₃ OCF₃ OCF₃

Formulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with an agriculturally suitable carrier comprising at leastone of a liquid diluent, a solid diluent or a surfactant. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature. Useful formulations include liquids such as solutions(including emulsifiable concentrates), suspensions, emulsions (includingmicroemulsions and/or suspoemulsions) and the like which optionally canbe thickened into gels. Useful formulations further include solids suchas dusts, powders, granules, pellets, tablets, films, and the like whichcan be water-dispersible (“wettable”) or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand  5-90  0-94  1-15 Water-soluble Granules, Tablets and Powders.Suspensions, Emulsions,  5-50 40-95  0-15 Solutions (includingEmulsifiable Concentrates) Dusts  1-25 70-99 0-5 Granules and Pellets0.01-99      5-99.99  0-15 High Strength Compositions 90-99  0-10 0-2

Typical solid diluents are described in Watkings, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenze sulfonates,organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalenesulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, silica, talc, diatomaceous earth, urea,calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.Liquid diluents include, for example, water, N,N,-dimethylformamide,dimethyl sulfoxide, N-alkypyrrolidone, ethylene glycol, polypropyleneglycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive,castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean,rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone,2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcoholssuch as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example.U.S. Pat. No. 3,060,084. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browing, “Agglomeration”, ChemicalEngineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer'sHandbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 andfollowing, and WO 91/13546. Pellets can be prepared as described in U.S.Pat. No. 4,172,714. Water-dispersible and water-soluble granules can beprepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos.5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught inGB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat.No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62and Examples 8, 12, 15, 39, 41, 52, 53, 132, 138-140, 162-164, 166, 167and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5,line 17 and Examples 1-4; Klingman, Weed Control as a Science, JohnWiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., WeedControl Handbook, 8th Ed., Blackwell Scientific Publications, Oxford,1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A.

Example A High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica  1.0%. Example B Wettable PowderCompound 1 65.0% dodecylphenol polyethylene glycol ether  2.0% sodiumligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite(calcined) 23.0%. Example C Granule Compound 1 10.0% attapulgitegranules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves)90.0%. Example D Extruded Pellet Compound 1 25.0% anhydrous sodiumsulfate 10.0% crude calcium ligninsulfonate  5.0% sodiumalkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite 59.0%.

Test results indicate that the compounds of the present invention arehighly active preemergent and postmergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpostemergence weed control in areas where complete control of allvegetation is desired such as around fuel storage tanks, industrialstorage areas, parking lots, drive-in theaters, air fields, river banks,irrigation and other waterways, around billboards and highway andrailroad structures. Some of the compounds are useful for the control ofselected grass and broadleaf weeds with tolerance to important agronomiccrops which include but are not limited to alfalfa, barley, cotton,wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats,peanuts, vegetables, tomato, potato, perennial plantation cropsincluding coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes,fruit trees, nut trees, banana, plantain, pineapple, hops, tea andforests such as eucalyptus and conifers (e.g. loblolly pine), and turfspecies (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescueand Bermuda grass). Those skilled in the art will appreciate that notall compounds are equally effective against all weeds. Alternatively,the subject compounds are useful to modify plant growth.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is 0.001 to 20 kg/ha with a preferred rangeof 0.004 to 1.0 kg/ha. One skilled in the art can easily determine theherbicidally effective amount necessary for the desired level of weedcontrol.

Compounds of this invention can be used alone or in combination withother commercial herbicides, insecticides or fungicides. Compounds ofthis invention can also be used in combination with commercial herbicidesafeners such as benoxacor, dichlormid and furilazole to increase safetyto certain crops. A mixture of one or more of the following herbicideswith a compound of this invention may be particularly useful for weedcontrol: acetochlor, acifluorfen and its sodium salt, aclonifen,acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole,ammonium sulfamate, anilofos, asulam, atrazine, azafenidin,azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and itssodium salt, bromacil bromoxynil, bromoxynil octanoate, butachlor,butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H),carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron,choridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron,chlorpropham, chlorsulfuron, chlorthal-dimethyl, cimmethylin,cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine,cyanazine, cycloate, cyslosulfamuron, 2,4-D and butotyl, butyl, isoctyland isopropyl esters and its dimethylammonium, diolamine and trolaminesalts, daimuroin, dalapon, dalapon-sodium, dazomet, 2,4-DB and itsdimethylammonium, potassium and sodium salts, desmedipham, desmetryn,dicamba and its diglycolammonium, dimethylammonium, potassium and sodiumsalts, dichlobenil, dichlorprop, diclofop-methyl,2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methyl-3-pyridine-carboxylicacid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate,dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine,diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC,esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate,ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron,fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin,flumetsulam, flumiclorac-pentlyl, flumioxazin, fluometuron,fluroglycofen-ethyl, flupoxam, flupysulfuron-methyl and its sodium salt,fluridone, flurochloridone, fluroxypyr, fluthiacet-methyl, fomesafen,fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate,glyphosate-isopropylammoinium, glyphosate-sesquisodium,glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl,haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr,imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium,imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon,isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleichydrazide, MCPA and its dimethylammonium, potassium and sodium salts,MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium,methabenzthiazuron, methylarsonic acid and its calcium, monoammonium,monosodium and disodium salts, methyl[[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate(AKH-7088), methyl5-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate(NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin,metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam,neburon, nicosuilfron, norflurazon, oryzalin, oxadiazon, oxasulfuron,oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone(KPP-314), perfluidone, phenmedipham, picloram, picloram-potassium,pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron,pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl,pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfiiron, sethoxydim,siduron, simazine, sulcotrione (ICIA0051), sulfentrazone,sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil,terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390),thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate,triasulfuron, triaziflam, tribenuron-methyl, triclopyr,triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin,triflusulfuron-methyl, and vernolate.

In certain instances, combinations with other herbicides having asimilar spectrum of control but a different mode of action will beparticularly advantageous for preventing the development of resistantweeds.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index TablesA-D for compound descriptions. The abbreviation “Ex.” stands for“Example” and is followed by a number indicating in which example thecompound is prepared.

INDEX TABLE A

Cmpd J R¹ R³ R⁴ A mp (° C.) 1 (Ex. 1)

CH₃ H H

112-113 2 (Ex. 2)

CH₃ H H

 90-92*  3

H H H

oil*  4

CH₃ H H

82-91  5

CH₃ H H

 98-100  6

CH₃ H H

112-114  7

CH₃ H H

84-89  8

CH₃ H H

solid* 9 (Ex. 3)

CH₃ H H

112-114 10

CH₃ H H

134-142 11

CH₃ H H

121-128 12

CH₃ H H

157-160 13

CH₃ H H

121-123 14

CH₃ H H

114-116 15

CH₃ H H

71-76 16

CH₃ H H

58-66 17

CH₃ CN H

156-157 18

CH₃ COOCH₃ H

127-129 19

CH₃ CH₃ H

102-104 20

CH₃ H OCH₃

78-82 21

CH₃ Cl H

105-109 22

CH₂CH₃ H H

73-75 23

OCH₃ H H

92-93 24

CH₃ H H

65-67 25

CH₃ H H

72-74 26

CH₃ H H

58-60 27

CH₃ H H

75-77 28

CH₃ H H

93-95 29

CH₃ H H

78-80 30

CH₃ H H

128-132 31

CH₃ H H

48-50 32

CH₃ H H

152-154 33

CH₃ H H

150-152 34

CH₃ H H

145-146 35

CH₃ H H

137-138 36

CH₃ H H

164 37

CH₃ H H

114-115 38

CH₃ H H

134-136 39

CH₃ H H

131-132 40

CH₃ H H

135-138 41

CH₂CH₃ H H

59-61 42

CH₃ H H

72-74 43

CH₃ H H

103-104 44

CH₃ H H

89-94 45

OCH₃ H H

80-85 46

CH₂CH₃ H H

76-77 47

CH₂CH₃ H H

oil* 48

CH₂CH₂CH₃ H H

49

CH₂CH₃ H H

oil* 50

CH₂CH₃ H H

oil* 51

CH₃ H H

104-106 52

CH₃ H H

93-97 53

CH₃ H H

150-152 54

CH₃ H H

139-141 55

CH₃ H H

100-102 56

CH₂CH₂CH₃ H H

81-84 57

CH₂CH₂CH₃ H H

63-65 58

CH₂CH₂CH₃ H H

oil* *See Index Table B for ¹H NMR data.

INDEX TABLE B Cmpd No. ¹H NMR Data (CDCl₃ solution unless indicatedotherwise)^(a)  2 δ 8.55(t,2H), 7.55-7.50(m,2H), 7.45-7.40(m,2H),6.72(d,IH), 4.26(s,2H), 2.32(s,3H).  3 δ 8.70(d,1H), 8.65(d,1H),7.60-7.55(m,2H), 7.50-7.45(m,2H), 7.05(d,1H), 6.75(d,1H), 4.28(s,2H).  8δ 8.62(s,1H), 8.27(m,2H), 7.7(s,1H), 7.47(m,3H), 7.4(s,1H), 5.28(s,2H),2.36(s,3H). 47 δ 8.59(m,2H), 7.40-7.10(m,4H), 6.71(d,1H), 4.24(s,2H),2.70(q,2H), 1.20(t,3H). 48 δ 8.56(s,2H), 7.34(t,1H), 7.15(m,3H),6.72(m,1H), 4.24(s,2H), 2.65(t,2H), 1.57(m,2H), 0.98(t,3H). 49 δ8.65(s,1H), 8.47(s,1H), 8.17(s,1H), 7.40-7.15(m,4H), 4.20(s,2H),2.70(q,2H), 1.25(t,3H). 50 δ 9.20(s,1H), 8.60(s,1H), 7.41(t,1H),7.15(m,3H), 4.25(s,2H), 2.80(q,2H), 1.24(t,3H.). 58 δ 8.57(s,1H),8.54(m,1H), 7.53(m,2H), 7.43(m,2H), 6.71(d,1H), 4.28(s,2H), 2.65(t,2H),1.61(m,2H), 0.98(t,3H).

INDEX TABLE C

Cmpd J R¹ A mp (° C.) 59 (Ex. 4)

CH₃

113-116 60

OCH₃

183-185 61

CH₃

80-82 62

CH₃

85-87 63

CH₃

oil* 64

CH₃

120-123 65

CH₃

144-146 66

CH₃

85-88 67

CH₃

oil* 68

CH₃

79-85 69

CH₂CH₃

95-99 70

H

oil* 71

CH₂CH₃

oil* 72

CH₂CH₃

150-153 73 (Ex. 5)

CH₃

159-161 74

CH₃

155-157 75

CH₃

122-123 76

H

62-64 77

H

 96-100 78

H

122-124 *See Index Table D for ¹H NMR data.

INDEX TABLE D Cmpd No. ¹H NMR Data (CDCl₃ solution unless indicatedotherwise)^(a) 63 δ 8.77(s,1H), 8.57(s,1H), 8.17(s,1H), 7.77-7.85(m,2H),7.50-7.60(m,2H), 2.42(s,3H). 67 δ (s,1H), 8.93(s,1H), 8.25(s,1H),8.07(d,1H), 7.97(d,1H), 7.68(m,1H), 2.48(s,3H). 70 δ 9.13(d,1H),8.60(m,2H), 8.42(d,1H), 7.91(m,2H), 7.72(t,1H), 6.70(d,1H). 71 δ8.81(s,1H), 8.58(s,1H), 8.18(s,1H), 7.81(s,1H), 7.77(m,1H), 7.57(m,2H),2.77(q,2H), 1.28(t,3H). ^(a 1)H NMR data are in ppm downfield fromtetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet,(t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets,(dt)-doublet of triplets, (br s)-broad singlet.

Biological Examples of the Invention

Test A

Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitariaspp.), morningglory (Ipomoea spp.), and velvetleaf (Abutilontheophrasti) were planted into a sandy loam soil and treatedpreemergence by soil drench with test chemicals formulated in anon-phytotoxic solvent mixture which includes a surfactant. At the sametime, these crop and weed species were also treated postemergencesprayed to runoff, with test chemicals formulated in the same manner.

Plants ranged in height from two to eighteen cm and were in the one totwo leaf stage for the postemergence treatment. Treated plants anduntreated controls were maintained in a greenhouse for approximatelyeleven days, after which all treated plants were compared to untreatedcontrols and visually evaluated for injury. Plant response ratings,summarized in Table A, are based on a 0 to 10 scale where 0 is no effectand 10 is complete control. A dash (−) response means no test results.

TABLE A COMPOUND Rate 2000 g/ha Rate 1000 g/ha PRE SOIL DRENCH 1 6 8 1213 59 65 73 74 8 Barnyardgrass 10 8 7 7 9 10 5 9 1 4 Crabgrass 10 9 10 910 10 8 10 7 9 Morningglory 8 5 8 3 3 9 4 9 1 9 Velvetleaf 9 8 3 5 9 104 9 4 2 COMPOUND Rate 1000 g/ha Rate 500 g/ha SPRAYED TO RUNOFF 1 6 8 1213 59 65 73 74 8 Barnyardgrass 9 8 3 5 6 9 4 8 5 3 Crabgrass 9 9 5 8 9 95 9 8 8 Morningglory 9 6 7 2 2 8 10 9 10 3 Velvetleaf 9 9 2 6 8 9 5 9 51

Test B

Seeds of bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides),broadleaf signalgrass (Brachiaria decumbens), cocklebur (Xanthiumstrumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giantfoxtail (Setaria faberii), lambsquarters (Chenopodium album),momingglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape(Brassica napus), soybean (Glycine max), sugar beet (Beta vulgaris),velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild oat(Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were plantedand treated preemergence with test chemicals formulated in anon-phytotoxic solvent mixture which included a surfactant.

At the same time, these crop and weed species were also treated withpostemergence applications of test chemicals formulated in the samemanner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) forpostemergence treatments. Plant species in the flood test consisted ofrice (Oryza sativa), smallflower flatsedge (Cyperus difformis), ducksalad (Heteranthera limosa) and bamyardgrass (Echinochloa crus-galli)grown to the 2-leaf stage for testing. Treated plants and controls weremaintained in a greenhouse for twelve to sixteen days, after which allspecies were compared to controls and visually evaluated. Plant responseratings, summarized in Table B, are based on a scale of 0 to 10 where 0is no effect and 10 is complete control. A dash (−) response means notest result.

TABLE B Rate 500 g/ha COMPOUND Postemergence 1 2 3 4 5 6 7 9 10 11 12 1314 16 32 52 53 54 59 61 62 63 64 65 66 67 68 73 74 B. signalgrass 9 — 33 5 — 1 9 3 7 7 8 4 1 — 9 2 5 3 5 3 5 8 1 5 9 5 8 2 Barnyardgrass — 6 68 3 3 2 8 4 — 3 3 6 4 4 8 2 4 8 4 4 3 5 0 4 6 4 4 0 Bedstraw 10 9 9 9 98 3 10 10 10 10 10 10 5 — 10 10 9 9 9 4 8 9 7 8 10 10 9 6 Blackgrass 9 93 7 5 2 1 9 3 5 4 5 3 3 — 9 6 3 6 8 4 6 9 0 6 10 5 9 1 Cocklebur 10 9 6— 8 7 — 9 9 9 8 9 7 6 — 9 6 9 8 8 7 8 9 2 5 9 7 8 5 Corn 7 7 3 4 4 3 2 53 3 3 4 3 1 — 7 1 3 4 4 2 2 5 1 3 7 2 3 1 Crabgrass 9 10 3 9 8 9 2 10 67 3 9 4 7 — 9 4 5 9 9 8 6 9 1 10 10 8 9 3 Ducksalad — 2 6 5 2 6 2 6 5 —2 3 3 2 6 9 7 3 7 5 2 6 9 0 7 8 3 3 0 Giant foxtail 9 10 5 8 6 6 1 9 5 94 5 3 3 — 9 2 4 9 9 3 3 5 1 4 9 3 9 1 Morningglory 10 9 8 9 4 8 5 10 9 —9 9 8 1 — 10 3 10 10 9 10 10 8 10 10 10 10 10 7 Nutsedge 2 2 0 0 0 3 0 33 — 0 0 0 1 — 7 — 0 0 — — — 2 — 1 — — — — Rape 9 10 7 10 10 8 7 10 9 109 9 7 5 — 10 9 9 7 9 3 8 4 2 7 9 7 10 3 Redroot pigweed 10 9 9 10 9 9 710 9 10 9 10 9 9 — 10 7 7 9 9 10 9 10 7 10 10 10 10 8 Rice — 6 6 7 3 3 08 3 — 3 1 5 4 2 7 2 4 6 2 0 1 3 0 2 4 3 3 0 S. Flatsedge — 9 9 8 5 7 4 99 — 8 5 9 3 7 9 9 9 9 9 8 9 9 0 9 9 7 3 0 Soybean 9 8 8 8 6 6 5 9 8 9 55 5 4 — 9 7 4 9 6 2 2 6 2 7 8 7 6 3 Sugarbeets 10 9 9 10 10 9 8 9 9 10 910 9 9 — 10 10 9 9 10 9 9 10 8 10 9 10 9 7 Velvetleaf 9 9 4 9 9 8 2 9 99 8 8 4 2 — 9 7 3 8 8 3 8 9 2 8 8 8 10 2 Wheat 5 5 3 2 4 3 0 6 3 3 4 4 31 — 8 2 2 3 4 3 2 5 2 3 6 4 6 2 Wild oats 9 7 3 3 5 3 0 8 3 5 5 4 3 1 —9 2 3 6 5 3 2 7 1 3 8 3 9 1 Rate 500 g/ha COMPOUND Preemergence 1 2 3 45 6 7 9 10 11 12 13 14 16 52 53 54 59 61 62 63 64 65 66 67 68 73 74 75B. signalgrass 9 — 5 — 9 9 0 10 4 8 9 9 5 7 10 6 6 9 9 9 9 10 2 10 10 1010 0 9 Bedstraw 9 10 5 8 7 5 0 9 10 9 8 6 2 1 10 8 4 8 9 6 8 9 0 8 10 610 0 8 Blackgrass 10 10 10 10 7 4 0 10 3 5 6 9 3 4 10 2 4 9 8 5 9 9 0 109 7 10 0 10 Cocklebur 10 3 0 1 — 0 0 9 3 — 3 7 — 0 10 1 0 2 10 0 1 7 0 35 8 — 0 9 Corn 2 2 1 2 1 0 0 4 1 0 2 2 3 0 8 0 1 3 2 2 2 4 0 3 7 1 2 0 2Crabgrass 10 10 5 10 9 10 2 10 9 10 10 10 8 8 10 8 8 10 10 10 9 10 0 910 10 10 1 10 Giant foxtail 10 10 10 10 10 10 5 10 9 10 9 10 9 8 10 6 1010 10 4 8 6 0 4 10 10 10 0 9 Morningglory 10 10 10 8 9 2 0 10 10 10 1010 8 1 10 5 2 10 10 7 10 10 5 9 10 9 10 0 10 Nutsedge 1 0 5 0 1 0 0 0 01 0 0 0 0 1 0 0 0 — 0 0 2 0 0 0 0 0 0 0 Rape 10 10 7 9 10 7 0 10 7 10 69 8 1 10 7 3 10 9 3 8 10 0 8 10 8 10 0 4 Redroot pigweed 10 10 10 10 106 2 10 7 10 9 9 4 8 10 8 9 10 10 10 10 10 0 10 10 10 10 0 10 Soybean 5 52 3 3 0 0 4 1 2 3 3 1 0 9 0 0 4 2 1 0 1 0 1 8 2 2 0 1 Sugarbeets 10 1010 10 10 10 1 10 10 10 10 10 9 9 10 9 9 10 10 10 10 10 0 10 10 10 10 010 Velvetleaf 10 10 6 7 9 3 0 9 8 10 4 10 7 1 10 8 1 10 10 7 10 10 1 810 8 8 0 10 Wheat 9 3 0 5 3 0 0 6 1 3 0 1 0 0 6 1 1 5 4 0 4 2 0 3 4 4 90 5 Wild oats 10 10 9 9 8 3 0 9 4 6 4 9 2 3 10 1 4 9 8 4 8 9 0 5 9 8 100 9 Rate 250 g/ha COMPOUND Postemergence 1 2 3 4 5 6 7 9 10 11 12 13 1415 16 17 18 19 20 21 22 23 24 25 B. signalgrass 8 — 3 2 4 — 1 9 3 4 7 73 8 1 7 3 2 3 7 7 9 3 3 Barnyardgrass — 5 6 8 3 2 1 7 3 — 3 3 5 9 4 6 23 0 4 6 6 4 5 Bedstraw 9 9 8 9 9 7 3 10 10 10 10 10 8 9 4 9 9 3 4 9 8 910 10 Blackgrass 9 7 3 6 5 2 — 8 3 7 4 5 3 9 2 7 2 1 3 6 9 9 4 8Cocklebur 9 8 5 7 8 7 — 10 9 9 8 9 7 10 5 8 8 3 7 8 8 10 10 9 Corn 4 6 33 2 3 2 5 3 3 3 3 3 5 1 3 2 3 3 4 4 3 1 3 Crabgrass 9 9 3 9 4 8 2 10 4 63 7 2 9 2 4 3 2 3 8 9 9 8 10 Ducksalad — 2 3 2 1 0 0 7 3 — 1 2 2 7 1 5 27 0 5 6 6 3 6 Giant foxtail 9 9 3 7 4 5 1 9 4 5 3 4 1 8 1 5 1 1 3 9 8 93 8 Morningglory 10 9 7 8 3 8 2 10 7 10 9 9 6 9 1 8 8 6 4 9 10 9 10 10Nutsedge 1 — 0 0 0 2 0 3 0 1 0 0 0 2 0 0 0 0 0 3 — — — 2 Rape 9 9 6 1010 8 6 10 9 10 9 9 6 9 2 8 9 3 5 10 10 10 10 10 Redroot pigweed 10 9 910 9 9 7 10 9 10 9 10 9 9 8 10 9 7 8 10 10 10 10 10 Rice — 5 4 6 2 2 0 72 — 3 0 5 7 3 6 0 2 0 5 5 5 2 5 S. Flatsedge — 8 9 7 5 7 2 9 9 — 8 4 8 92 5 2 6 0 9 9 9 3 7 Soybean 9 8 7 8 5 6 3 10 8 8 5 5 5 9 4 8 6 4 6 6 8 86 7 Sugarbeets 10 9 9 9 10 8 8 10 9 10 8 10 8 10 9 10 9 6 7 10 10 10 1010 Velvetleaf 9 9 3 8 7 8 1 10 8 8 8 8 4 8 2 7 7 2 7 9 9 9 7 9 Wheat 3 32 2 3 2 0 4 3 3 3 3 2 6 0 4 3 0 3 5 6 5 3 4 Wild oats 7 6 2 3 4 3 0 6 23 4 4 3 9 1 5 5 2 3 6 8 9 4 4 Rate 250 g/ha COMPOUND Postemergence 26 2728 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 49 50 B.signalgrass 2 5 9 5 2 5 2 2 1 1 1 0 1 1 1 6 7 6 5 0 5 8 4 2Barnyardgrass 2 3 5 4 4 5 3 3 1 2 0 0 0 0 2 5 5 5 4 0 4 6 6 4 Bedstraw 69 8 9 6 6 10 9 7 8 7 — — 4 6 10 — 10 9 0 10 — — — Blackgrass 1 5 8 5 1 45 2 1 1 2 0 0 1 2 8 7 8 7 0 6 6 6 8 Cocklebur 3 9 8 8 8 7 9 6 8 2 3 3 85 5 9 9 9 9 0 9 8 9 7 Corn 1 3 4 3 2 2 1 1 1 1 1 1 1 1 1 3 8 5 3 0 3 4 42 Crabgrass 1 6 10 9 7 9 2 1 1 2 1 1 1 1 3 10 8 10 7 0 8 10 9 6Ducksalad 0 2 6 4 5 6 4 2 0 1 1 0 0 0 7 5 8 9 9 0 4 7 4 8 Giant foxtail1 4 9 4 2 3 2 1 1 1 1 1 0 1 2 9 9 9 9 0 7 7 5 2 Morningglory 3 8 3 10 94 10 5 2 1 2 1 1 1 5 8 9 10 10 0 10 8 9 3 Nutsedge — — — — 2 — 1 0 0 0 00 0 0 — 0 2 3 3 — — — — 2 Rape 6 9 10 9 10 9 8 7 3 9 5 4 6 4 8 10 10 1010 0 9 10 9 10 Redroot pigweed 8 10 10 10 9 9 9 7 6 5 8 7 5 3 6 10 9 1010 0 10 9 9 9 Rice 0 1 3 3 2 3 2 3 1 1 0 0 0 0 2 6 6 7 7 0 4 6 5 4 S.Flatsedge 2 5 8 8 8 8 6 8 3 2 6 0 4 2 5 9 9 9 9 0 7 9 9 9 Soybean 5 7 77 6 7 6 4 2 2 2 0 1 2 2 7 9 9 6 0 9 7 7 7 Sugarbeets 8 10 10 10 10 10 1010 9 10 9 5 9 10 10 10 10 10 10 0 10 9 9 10 Velvetleaf 2 7 8 4 8 4 9 6 11 1 1 2 1 2 8 9 9 9 0 9 8 9 8 Wheat 0 4 5 4 2 4 2 1 1 1 2 0 1 1 2 3 4 53 0 4 6 5 4 Wild oats 0 5 6 4 2 4 3 3 2 2 2 0 1 1 1 7 6 6 5 0 4 9 7 4Rate 250 g/ha COMPOUND Postemergence 51 52 53 54 59 60 61 62 63 64 65 6667 68 70 71 72 73 74 75 76 77 78 B. signalgrass 9 9 2 4 2 3 4 2 4 6 1 47 3 1 — 6 9 1 3 0 1 1 Barnyardgrass 7 7 2 3 5 2 3 3 3 4 0 4 5 4 0 3 6 60 3 0 0 0 Bedstraw 10 10 10 7 8 3 9 3 5 7 7 6 10 9 1 — 4 9 2 9 0 4 0Blackgrass 9 9 1 2 5 2 6 2 3 7 0 5 9 4 0 — 5 9 0 8 0 2 1 Cocklebur 9 9 67 7 4 8 7 — 7 1 4 8 7 2 — 4 9 5 7 4 3 0 Corn 9 6 1 3 3 3 3 2 2 4 1 2 6 22 — 5 3 1 3 1 1 2 Crabgrass 10 9 4 5 8 4 7 5 4 9 1 8 10 8 1 — 8 9 1 — 12 0 Ducksalad 9 9 5 1 6 2 3 0 2 6 0 5 6 2 0 2 3 2 0 2 0 0 0 Giantfoxtail 10 9 1 4 8 2 5 2 3 4 1 2 9 2 0 — 7 9 1 4 1 1 0 Morningglory 1010 — 3 10 9 — 9 10 8 8 9 10 10 2 — 4 9 7 10 1 4 2 Nutsedge — — 0 0 0 0 0— 0 0 0 1 4 0 0 — — 2 0 0 — — 0 Rape 10 9 8 9 7 4 8 2 8 4 2 7 8 — 1 — 710 1 9 2 2 0 Redroot pigweed 10 10 7 6 8 7 9 9 9 10 6 10 10 10 3 — 9 108 10 2 3 4 Rice 8 7 1 3 4 1 2 0 1 2 0 1 2 3 0 2 2 6 0 1 0 0 0 S.Flatsedge 9 9 9 9 8 6 8 7 8 8 0 8 9 7 0 4 4 6 0 1 0 0 0 Soybean 10 9 7 48 2 5 1 2 5 2 6 8 7 3 — 5 9 2 3 1 1 0 Sugarbeets 10 10 10 9 9 9 10 9 910 8 10 9 10 2 — 9 9 6 10 3 3 0 Velvetleaf 9 8 7 3 7 2 8 2 8 8 2 6 8 7 1— 5 9 2 9 1 1 0 Wheat 9 7 1 2 2 3 3 2 2 3 2 2 5 2 0 — 4 5 1 3 0 0 0 Wildoats 9 8 1 3 3 2 3 1 2 5 1 2 8 2 0 — 4 9 1 3 0 1 0 Rate 250 g/haCOMPOUND Preemergence 1 2 3 4 5 6 7 9 10 11 12 13 14 15 16 17 18 19 2021 22 23 24 25 B. signalgrass 9 — 2 — 9 9 0 10 2 8 8 9 0 9 3 9 2 0 4 8 99 6 6 Bedstraw 8 10 5 8 7 0 0 10 7 9 4 5 0 8 0 5 5 0 1 8 7 9 1 2Blackgrass 10 10 4 10 7 0 0 10 2 5 6 4 0 10 2 9 1 0 4 5 9 9 3 8Cocklebur 3 1 0 0 1 0 0 9 1 3 2 5 0 — 0 0 0 0 — 0 2 3 0 8 Corn 2 1 0 1 00 0 3 0 0 0 1 0 2 0 1 0 0 0 1 2 1 0 0 Crabgrass 10 10 2 8 9 8 1 10 9 9 810 7 10 2 9 6 0 2 10 10 10 1 1 Giant foxtail 10 10 9 10 10 9 1 10 8 9 910 7 10 7 10 — 0 1 9 10 10 6 9 Morningglory 10 10 4 8 8 2 0 10 9 9 10 92 9 0 2 6 0 0 6 10 10 4 10 Nutsedge — 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 00 0 — — 0 0 Rape 10 10 2 7 10 4 0 10 4 10 6 9 2 9 0 3 0 0 0 5 10 7 4 10Redroot pigweed 10 10 10 10 8 6 2 10 7 10 9 9 4 10 8 10 7 0 1 9 10 10 109 Soybean 3 2 0 1 2 0 0 2 1 1 3 3 0 1 0 0 0 0 0 0 2 1 0 1 Sugarbeets 1010 10 10 10 9 0 10 6 10 10 10 6 10 7 9 6 0 2 10 10 10 9 9 Velvetleaf 108 5 7 9 2 0 9 8 8 4 10 1 7 1 1 0 0 0 10 8 10 2 2 Wheat 8 3 0 1 2 0 0 5 01 0 0 0 7 0 3 0 0 0 2 4 6 0 2 Wild oats 9 9 7 8 6 2 0 9 2 4 4 7 0 9 2 85 0 3 8 9 9 4 5 Rate 250 g/ha COMPOUND Postemergence 26 27 28 29 30 3132 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 49 50 B. signalgrass 1 39 4 6 9 7 1 1 0 0 0 1 0 1 7 10 9 8 0 9 9 5 1 Bedstraw 0 — 8 3 10 — 10 20 1 0 0 2 0 — 8 8 10 10 0 10 8 8 9 Blackgrass 0 4 6 3 2 3 4 0 0 0 1 0 00 2 10 10 8 9 0 10 10 6 10 Cocklebur 0 — — 0 0 — 0 0 0 0 0 0 — 0 0 0 8 28 0 — 2 2 0 Corn 0 0 1 0 0 1 0 0 0 0 0 0 0 0 0 1 2 1 1 0 3 3 1 0Crabgrass 1 5 10 7 8 10 3 0 1 1 0 0 0 0 0 9 10 10 9 0 10 10 9 9 Giantfoxtail 1 9 10 9 9 10 5 1 1 1 0 0 1 0 3 10 10 9 9 0 10 10 9 8Morningglory 0 2 3 3 3 2 3 0 0 0 0 0 0 0 2 2 10 10 10 0 10 6 4 4Nutsedge — 0 0 — 0 0 0 — 0 0 0 0 0 0 0 — 0 — — 0 0 — — — Rape 0 3 4 1 31 10 2 0 0 1 0 0 0 2 4 10 10 10 0 10 10 10 10 Redroot pigweed 4 7 7 3 103 10 2 2 5 8 0 0 0 2 10 10 10 10 0 10 10 10 9 Soybean 0 0 1 0 0 0 1 0 00 1 0 0 0 0 1 4 7 2 0 7 2 1 1 Sugarbeets 0 8 3 4 10 3 10 4 0 1 2 0 0 0 68 10 10 10 0 10 9 9 10 Velvetleaf 0 1 2 0 6 0 10 1 0 1 1 0 0 0 1 10 1010 10 0 10 10 8 9 Wheat 0 1 0 0 0 0 0 1 0 0 0 0 0 0 0 2 4 2 3 0 5 5 4 2Wild oats 0 3 4 1 2 2 4 1 0 1 0 0 0 0 1 9 9 9 9 0 9 10 7 8 Rate 250 g/haCOMPOUND Preemergence 51 52 53 54 59 60 61 62 63 64 65 66 67 68 70 72 7374 75 76 77 78 B. signalgrass 9 10 2 3 9 3 8 8 8 10 1 9 10 9 0 7 9 0 9 00 0 Bedstraw 9 9 7 1 6 1 6 2 4 8 0 3 9 6 0 5 9 0 6 — — 0 Blackgrass 1010 1 3 7 2 5 1 8 6 0 8 8 7 0 4 10 0 9 0 0 0 Cocklebur 10 7 0 0 — 0 1 — —— 0 0 2 2 0 0 7 0 2 0 0 0 Corn 8 7 0 1 1 0 1 1 1 4 0 1 4 1 0 5 2 0 1 0 00 Crabgrass 10 10 6 3 10 6 8 9 8 10 0 9 10 9 0 9 10 0 9 0 1 0 Giantfoxtail 10 10 6 8 10 5 10 4 6 5 0 2 10 9 0 7 10 0 5 0 1 0 Morningglory10 10 2 2 10 5 10 4 10 10 0 3 10 5 0 8 9 0 10 0 1 0 Nutsedge — — 0 0 0 —0 0 — — 0 — — 0 — — 0 0 0 — — 0 Rape 10 10 7 3 7 1 9 2 4 8 0 4 10 4 0 96 0 4 0 0 0 Redroot pigweed 10 10 7 7 10 10 9 10 10 10 0 9 10 10 0 9 100 10 0 0 0 Soybean 9 8 0 0 2 0 1 0 0 1 0 0 3 2 0 3 1 0 0 0 0 0Sugarbeets 10 10 9 7 10 9 10 10 10 10 0 10 10 10 0 10 10 0 10 0 0 0Velvetleaf 10 10 4 1 9 1 10 2 10 6 0 8 10 7 0 7 7 0 9 0 3 0 Wheat 5 3 00 3 0 4 0 3 1 0 2 3 2 0 3 7 0 4 0 0 0 Wild oats 8 9 1 3 9 0 7 4 5 5 0 56 7 0 3 10 0 7 0 0 0 Rate 125 g/ha COMPOUND Postemergence 1 2 3 4 5 6 79 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 B. signalgrass 6 — 3 24 — 1 8 3 3 5 5 2 4 1 5 2 2 2 4 7 5 2 3 Barnyardgrass — 4 4 8 2 1 1 5 2— 2 2 5 8 3 4 1 2 0 4 5 5 3 4 Bedstraw 9 9 8 8 9 7 3 10 9 9 9 9 4 9 4 98 3 4 9 8 9 10 10 Blackgrass 7 6 2 4 4 2 0 8 1 3 3 3 2 9 1 6 2 1 2 4 8 73 4 Cocklebur 8 8 3 6 7 6 — 9 8 8 8 9 7 9 4 8 7 3 5 8 8 10 9 9 Corn 4 42 2 2 3 1 4 2 3 2 3 2 4 1 2 2 2 3 3 3 3 1 2 Crabgrass 9 9 2 7 3 8 0 9 24 3 4 2 9 2 4 2 2 3 6 9 9 8 7 Ducksalad — 0 3 0 0 0 0 6 1 — 1 1 2 6 0 52 2 0 4 4 4 2 4 Giant foxtail 7 9 2 3 2 4 1 5 2 4 3 3 1 7 1 4 1 0 2 8 65 2 6 Morningglory 8 9 7 8 3 8 1 10 7 10 9 7 6 8 1 8 8 3 4 8 10 9 10 10Nutsedge — 0 0 0 0 — 0 1 0 1 0 0 0 2 0 0 0 0 0 2 0 0 1 1 Rape 9 9 6 10 98 5 10 9 9 9 8 6 9 2 8 7 2 4 10 10 10 10 10 Redroot pigweed 9 9 9 9 9 73 10 9 10 9 9 9 9 6 10 6 5 7 9 10 10 10 10 Rice — 4 4 2 1 2 0 6 2 — 2 04 7 1 4 0 0 0 4 4 4 1 4 S. Flatsedge — 5 9 6 3 5 1 9 9 — 6 4 8 8 2 3 1 20 8 8 8 1 5 Soybean 8 7 7 7 3 6 3 9 6 7 5 5 4 9 3 3 4 3 5 6 7 8 6 7Sugarbeets 10 9 9 9 10 8 3 10 8 10 8 10 8 9 8 10 7 4 5 9 10 10 10 10Velvetleaf 8 9 2 6 7 7 1 10 7 8 7 4 4 8 2 4 6 2 6 8 8 9 6 9 Wheat 2 2 22 2 2 0 3 3 2 3 3 0 4 0 3 3 0 3 4 4 4 2 4 Wild oats 7 3 2 2 4 3 0 4 2 33 3 1 7 0 4 5 1 3 5 6 6 3 3 Rate 125 g/ha COMPOUND Postemergence 26 2728 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 49 50 B.signalgrass 1 5 5 3 2 3 2 1 1 1 1 0 1 1 1 3 7 4 4 0 4 5 3 1Barnyardgrass 0 2 4 3 3 3 3 2 0 2 0 0 0 0 2 5 4 4 4 0 3 3 5 4 Bedstraw 39 8 9 6 6 6 9 3 6 7 1 7 3 4 9 9 10 9 0 9 — — 10 Blackgrass 1 4 5 3 1 2 21 1 1 0 0 0 1 2 6 7 6 5 0 5 5 6 5 Cocklebur 2 7 8 6 8 6 8 6 2 2 2 2 7 22 8 9 7 9 0 9 8 7 4 Corn 1 3 3 2 2 2 1 1 1 1 1 1 1 1 1 2 3 4 3 0 2 3 3 2Crabgrass 1 4 9 6 1 8 2 0 1 2 1 0 0 0 1 9 7 8 4 0 6 9 6 2 Ducksalad 0 13 3 4 2 3 1 0 0 0 0 0 0 5 3 8 9 7 0 1 3 4 5 Giant foxtail 1 4 4 4 1 3 10 1 1 1 0 1 1 0 6 7 9 7 0 4 4 5 2 Morningglory 3 8 3 10 5 3 8 5 1 1 2 11 1 2 8 9 9 — 0 10 6 6 3 Nutsedge 0 — 3 0 0 0 0 0 0 0 0 0 0 0 — 0 0 2 20 — — — 2 Rape 6 8 9 9 8 8 8 7 3 6 5 3 3 1 6 10 10 10 10 0 9 10 9 10Redroot pigweed 6 9 9 10 9 9 9 2 3 3 4 1 4 2 3 10 9 10 10 0 9 9 9 8 Rice0 1 2 2 1 2 1 1 1 1 0 0 0 0 1 5 6 6 6 0 2 5 4 3 S. Flatsedge 1 5 8 6 6 75 7 2 2 5 0 3 2 4 7 9 9 9 0 5 7 4 8 Soybean 3 5 7 4 3 4 5 2 2 2 1 0 1 12 7 9 9 6 0 8 8 7 7 Sugarbeets 8 9 9 9 10 10 10 10 8 10 8 5 9 9 10 10 1010 10 0 10 9 9 8 Velvetleaf 1 7 4 3 6 2 8 4 1 1 1 0 1 1 2 8 9 9 8 0 9 78 7 Wheat 0 4 4 3 2 3 2 1 1 0 1 0 1 1 1 3 3 4 3 0 3 5 5 3 Wild oats 0 45 2 2 3 3 2 1 1 1 0 1 1 0 5 6 5 4 0 4 8 6 3 Rate 125 g/ha COMPOUNDPostemergence 51 52 53 54 59 60 61 62 63 64 65 66 67 68 69 70 71 72 7374 75 76 77 78 B. signalgrass 8 9 1 3 2 2 4 2 3 5 1 3 7 3 3 0 2 4 9 1 20 0 0 Barnyardgrass 6 6 2 3 4 1 3 2 3 3 0 3 3 3 2 0 2 3 5 0 2 0 0 0Bedstraw 10 10 8 4 7 3 8 3 2 4 3 3 9 6 9 1 — — 9 1 9 0 1 0 Blackgrass 99 1 1 3 1 4 1 3 5 0 3 8 3 3 0 3 5 7 0 6 0 0 0 Cocklebur 9 8 5 3 7 3 7 53 7 1 4 7 — 8 2 4 4 9 5 7 3 3 0 Corn 8 5 1 2 2 2 3 2 2 3 1 2 5 1 2 1 3 33 1 3 1 1 0 Crabgrass 10 8 2 4 6 3 3 3 3 5 1 7 9 8 4 1 3 6 9 0 4 0 2 0Ducksalad 9 9 2 0 4 2 1 0 0 6 0 3 4 1 1 0 0 2 1 0 1 0 0 0 Giant foxtail10 8 1 3 6 2 4 2 2 3 1 2 6 2 3 0 2 6 8 0 2 0 1 0 Morningglory 10 10 3 3— 4 9 4 4 8 1 4 7 8 10 1 6 4 9 1 10 0 4 0 Nutsedge — 3 0 0 0 0 0 0 — 0 01 2 0 — 0 — — 0 0 0 — — 0 Rape 9 9 8 8 7 3 7 2 4 4 1 3 8 6 8 1 7 7 10 17 2 1 0 Redroot pigweed 10 10 6 5 8 7 9 9 9 9 3 9 10 10 10 2 8 9 9 2 9 12 0 Rice 5 5 1 2 3 0 0 0 0 1 0 1 2 1 2 0 2 0 5 0 1 0 0 0 S. Flatsedge 99 8 8 7 5 7 6 7 8 0 8 8 7 4 0 2 3 3 0 0 0 0 0 Soybean 9 9 5 3 7 2 5 1 23 2 5 7 5 4 2 4 2 9 2 3 0 1 0 Sugarbeets 10 10 10 7 9 8 10 9 9 10 7 10 910 10 1 8 9 10 2 10 2 1 0 Velvetleaf 8 8 6 2 7 2 7 2 8 7 1 5 8 7 8 1 6 39 1 9 1 1 0 Wheat 9 7 1 2 2 3 3 2 2 3 1 2 4 2 4 0 4 3 4 1 2 0 0 0 Wildoats 9 8 1 2 1 2 3 1 2 4 1 2 7 2 3 0 2 2 7 1 3 0 0 0 Rate 125 g/haCOMPOUND Preemergence 1 2 3 4 5 6 7 9 10 11 12 13 14 15 16 17 18 19 2021 22 23 24 25 B. signalgrass 9 — 2 — 8 4 0 9 1 3 8 8 0 9 2 7 1 0 1 3 99 3 2 Bedstraw 8 10 0 3 4 0 0 7 7 8 4 2 0 8 0 3 2 0 0 1 7 8 1 1Blackgrass 9 7 3 9 3 0 0 9 2 3 4 4 0 10 0 6 0 0 2 3 9 9 2 5 Cocklebur 21 0 0 0 0 0 2 — — — — — 1 0 0 — — 0 0 1 1 0 0 Corn 1 1 0 0 0 0 0 1 0 0 01 0 1 0 0 0 0 0 0 0 1 0 0 Crabgrass 10 10 1 6 9 2 0 10 7 7 4 10 1 10 0 80 0 1 6 10 10 3 0 Giant foxtail 10 10 8 10 9 6 0 10 7 9 7 10 4 10 3 10 00 0 8 10 10 6 4 Morningglory 10 9 3 7 4 1 0 10 3 8 6 10 0 7 0 1 4 0 0 110 8 4 3 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 1 0 0 0 Rape10 10 1 4 10 2 0 9 4 9 5 6 1 9 0 2 0 0 0 3 7 3 2 7 Redroot pigweed 10 109 8 8 3 0 10 6 9 9 9 2 10 0 9 3 0 0 8 10 9 8 3 Soybean 1 1 0 0 1 0 0 1 01 2 1 0 1 0 0 0 0 0 0 1 1 0 0 Sugarbeets 10 10 8 8 10 3 0 10 — 10 8 10 510 1 8 6 0 0 8 9 8 3 8 Velvetleaf 10 6 1 6 7 2 0 8 7 6 4 7 0 7 0 1 0 0 08 8 3 1 0 Wheat 5 2 0 0 2 0 0 2 0 1 0 0 0 4 0 1 0 0 0 0 2 3 0 1 Wildoats 9 9 4 7 5 0 0 8 1 4 2 5 0 9 1 5 3 0 2 5 8 8 1 3 Rate 125 g/haCOMPOUND Preemergence 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 4243 44 45 46 47 49 50 B. signalgrass 0 1 5 3 4 9 6 1 0 0 0 0 0 0 0 6 9 98 0 9 6 1 1 Bedstraw 0 0 4 1 10 — 8 1 0 0 0 0 1 0 — 2 8 9 5 0 9 8 7 7Blackgrass 0 2 5 1 2 2 2 0 0 0 0 0 0 0 1 9 10 5 6 0 8 8 4 5 Cocklebur 0— 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 5 0 — 2 0 0 Corn 0 0 0 0 0 0 0 0 0 0 00 0 0 0 1 1 1 1 0 1 2 1 0 Crabgrass 0 2 4 4 3 4 1 0 0 1 0 0 0 0 0 9 1010 4 0 9 10 7 9 Giant foxtail 1 5 9 4 5 5 2 1 0 0 0 0 1 0 1 9 10 9 5 0 910 8 7 Morningglory 0 2 2 2 1 2 2 0 0 0 0 0 0 0 1 1 10 10 9 0 10 6 3 3Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — — — 0 — 0 0 — — — Rape 0 2 2 1 20 10 0 0 0 0 0 0 0 1 3 10 10 8 0 9 9 8 10 Redroot pigweed 0 6 6 3 7 2 100 0 0 0 0 0 0 1 10 10 10 9 0 10 9 8 9 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 00 0 0 4 5 2 0 3 0 1 1 Sugarbeets 0 1 2 3 9 0 10 1 0 0 0 0 0 0 6 6 10 1010 0 10 7 6 6 Velvetleaf 0 0 1 0 2 0 9 0 0 0 0 0 0 0 0 3 7 10 10 0 10 108 7 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 1 0 3 3 4 2 Wild oats 0 13 0 1 1 3 0 0 0 0 0 0 0 0 9 8 9 7 0 8 9 6 4 Rate 125 g/ha COMPOUNDPreemergence 51 52 53 54 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 7475 76 77 78 B. signalgrass 9 9 1 1 9 3 7 4 7 9 0 9 9 8 9 0 2 2 9 0 9 0 00 Bedstraw 10 8 3 0 6 0 4 1 4 8 0 2 9 5 9 0 1 — 8 0 6 — — 0 Blackgrass 98 0 1 3 1 3 1 3 6 0 3 4 5 4 0 2 1 9 0 8 0 0 0 Cocklebur 10 — 0 0 2 0 0 0— 1 0 0 — — 2 0 0 0 1 0 0 0 0 0 Corn 8 3 0 0 1 0 1 0 1 3 0 1 4 1 0 0 1 41 0 0 0 0 0 Crabgrass 10 10 4 0 9 2 5 3 6 10 0 9 9 4 9 0 2 9 10 0 9 0 00 Giant foxtail 10 9 5 1 10 2 9 2 3 2 0 1 9 6 8 0 2 5 10 0 5 0 0 0Morningglory 10 10 2 1 6 2 3 2 7 10 0 3 10 3 8 0 4 3 9 0 10 0 0 0Nutsedge 9 — 0 0 0 0 0 0 0 — 0 — — 0 0 0 — — 0 0 0 0 — 0 Rape 10 10 5 07 0 8 1 3 4 0 0 9 3 8 0 7 5 6 0 3 0 0 0 Redroot pigweed 10 10 2 2 10 9 99 9 9 0 9 10 9 10 0 8 9 10 0 10 0 0 0 Soybean 9 7 0 0 2 0 1 0 0 1 0 0 21 1 0 0 3 1 0 0 0 0 0 Sugarbeets 10 10 8 1 10 8 10 10 10 10 0 10 10 10 90 3 10 9 0 10 0 0 0 Velvetleaf 10 10 2 0 7 1 10 2 2 6 0 4 9 7 8 0 6 4 40 8 0 0 0 Wheat 3 2 0 0 2 0 3 0 2 0 0 1 3 1 1 0 3 0 4 0 4 0 0 0 Wildoats 7 5 0 1 8 0 5 3 3 4 0 4 5 6 7 0 3 2 9 0 7 0 0 0 Rate 62 g/haCOMPOUND Postemergence 1 2 4 5 6 9 10 11 12 13 14 15 16 17 18 19 20 2122 23 24 25 26 27 B. signalgrass 3 — 1 3 — 5 2 3 4 5 2 4 1 4 2 1 2 3 5 42 2 1 3 Barnyardgrass — 3 4 2 0 5 1 — 2 2 4 6 2 4 2 0 0 3 4 4 2 3 0 1Bedstraw 9 9 6 6 5 10 8 8 7 7 4 9 3 8 7 2 4 5 — 9 4 9 1 8 Blackgrass 7 33 3 0 3 1 2 2 3 1 6 1 3 2 1 2 3 5 6 2 3 0 4 Cocklebur 7 8 5 5 5 9 6 7 —6 4 9 4 4 6 2 4 7 8 9 9 9 2 7 Corn 4 2 2 2 3 3 2 3 2 3 2 3 1 2 2 1 3 3 32 1 1 1 2 Crabgrass 4 8 4 2 5 9 2 2 2 3 2 9 2 4 1 1 2 3 9 7 8 7 1 3Ducksalad — 0 0 0 0 4 1 — 0 0 2 6 0 3 1 0 0 3 3 2 0 3 0 0 Giant foxtail3 7 2 2 — 4 2 2 2 2 1 7 1 2 1 0 2 1 6 2 2 3 1 3 Morningglory 4 8 8 3 310 5 7 9 7 2 8 — 7 3 3 3 8 10 6 8 10 3 5 Nutsedge — 0 0 0 2 0 0 1 0 0 00 0 0 0 0 0 2 0 0 0 1 0 2 Rape 9 9 9 8 8 9 8 9 7 6 5 9 1 7 4 2 3 9 10 108 10 3 8 Redroot pigweed 9 7 8 9 5 10 9 9 9 9 8 9 5 9 6 2 5 8 10 9 9 106 7 Rice — 3 2 1 1 5 0 — 1 0 4 6 1 4 1 0 0 3 3 3 1 3 0 0 S. Flatsedge —3 5 3 3 8 6 — 4 2 8 7 1 2 9 0 0 6 3 4 0 3 0 5 Soybean 8 6 6 3 6 8 6 5 34 4 9 3 3 3 2 4 6 6 8 3 4 3 5 Sugarbeets 10 9 9 9 7 10 8 9 7 9 7 9 8 9 72 3 9 10 10 10 10 3 9 Velvetleaf 7 8 5 6 7 10 6 8 7 4 3 5 1 2 5 1 4 7 89 2 8 1 5 Wheat 2 2 1 2 1 3 2 2 3 2 0 4 0 3 1 0 2 4 4 3 2 2 0 3 Wildoats 4 3 2 3 0 3 2 2 3 3 0 6 0 3 3 0 2 4 5 5 2 3 0 3 Rate 62 g/haCOMPOUND Postemergence 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 4344 45 46 47 49 50 51 52 B. signalgrass 4 3 1 3 1 1 1 1 1 0 1 1 1 2 6 4 30 3 4 2 1 2 4 Barnyardgrass 3 2 3 2 2 1 0 0 0 0 0 0 2 5 4 4 3 0 2 2 5 35 5 Bedstraw 2 2 1 4 6 9 2 6 6 1 7 3 4 9 9 9 8 0 8 9 9 9 9 9 Blackgrass4 2 0 2 1 0 0 1 0 0 0 1 2 5 6 5 4 0 4 5 5 2 7 5 Cocklebur 7 6 5 6 8 3 22 1 1 4 2 5 7 9 — 8 0 8 7 7 4 6 8 Corn 2 2 1 2 1 1 1 1 1 1 1 1 1 2 3 3 30 2 3 3 1 7 4 Crabgrass 3 4 1 4 1 0 0 2 0 0 0 0 1 7 4 7 3 0 6 7 5 1 9 6Ducksalad 2 1 3 1 2 0 0 0 0 0 0 0 1 2 1 8 4 0 1 3 4 4 8 9 Giant foxtail3 3 1 2 1 0 0 1 0 0 0 0 0 2 6 8 2 0 3 4 2 1 8 7 Morningglory 3 8 2 3 7 21 1 1 1 1 1 2 8 8 9 10 0 9 6 2 3 10 10 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0— 0 0 0 1 0 2 — — 2 7 1 Rape 9 8 4 8 8 6 2 6 4 1 3 1 6 10 10 9 9 0 9 109 9 9 9 Redroot pigweed 8 8 7 8 6 1 1 3 0 1 2 2 2 9 9 10 9 0 9 9 9 8 109 Rice 2 1 1 1 1 1 1 0 0 0 0 0 1 5 4 4 5 0 1 3 3 2 3 3 S. Flatsedge 5 14 4 2 3 2 1 2 0 0 0 2 5 9 9 9 0 4 7 4 6 9 9 Soybean 4 3 3 4 4 1 1 1 1 01 1 2 5 9 8 5 0 8 8 6 6 9 9 Sugarbeets 9 9 10 10 9 10 8 9 8 1 9 7 10 1010 10 10 0 10 9 9 7 10 9 Velvetleaf 3 3 5 2 4 1 1 1 1 0 1 0 1 8 8 8 8 09 7 8 6 7 8 Wheat 3 2 1 1 1 0 0 0 0 0 1 0 1 2 2 3 3 0 3 5 4 3 6 4 Wildoats 4 1 1 2 1 1 0 1 0 0 1 1 0 4 6 4 4 0 3 6 5 2 8 6 Rate 62 g/haCOMPOUND Postemergence 53 54 59 60 61 62 63 64 65 66 67 68 69 70 71 7273 74 75 76 77 78 B. signalgrass 1 3 2 2 3 2 4 4 1 2 5 2 3 0 2 2 8 1 2 00 0 Barnyardgrass 1 2 3 1 2 1 1 2 0 3 3 2 1 0 2 2 4 0 2 0 0 0 Bedstraw 53 7 2 8 3 2 3 0 2 9 5 9 1 — — 9 1 5 0 1 0 Blackgrass 1 1 2 1 3 1 2 4 0 25 2 2 0 2 4 7 0 3 0 0 0 Cocklebur 5 3 4 3 3 2 1 6 1 3 7 3 8 1 4 3 9 1 71 1 0 Corn 1 2 1 2 2 1 0 1 1 1 4 1 2 1 2 2 2 1 2 1 1 0 Crabgrass 1 2 6 23 2 3 4 1 2 7 5 3 0 2 4 7 0 — 0 0 0 Ducksalad 0 0 3 1 0 0 0 4 0 2 3 0 00 0 2 1 0 0 0 0 0 Giant foxtail 1 2 6 2 2 1 2 1 1 2 5 1 2 0 2 5 6 0 1 00 0 Morningglory — 2 7 2 5 3 2 2 — 2 7 2 9 1 1 — 9 1 10 0 2 0 Nutsedge 00 0 0 0 0 0 0 0 0 0 0 2 0 — — 0 0 0 — 0 0 Rape 8 7 6 3 6 2 3 3 1 3 6 6 60 5 3 10 1 5 1 1 0 Redroot pigweed 2 4 8 5 8 8 8 8 2 8 9 9 10 0 8 8 9 29 1 2 0 Rice 1 1 2 0 0 0 0 1 0 0 1 0 0 0 2 0 5 0 1 0 0 0 S. Flatsedge 56 7 4 3 3 4 8 0 6 5 5 2 0 0 3 3 0 0 0 0 0 Soybean 5 0 6 2 4 1 0 2 1 5 73 4 1 3 2 8 2 3 0 0 0 Sugarbeets 9 6 9 8 9 9 10 9 7 10 9 10 10 0 8 9 101 10 1 1 0 Velvetleaf 6 2 6 2 7 2 2 2 1 4 8 6 8 0 3 2 9 1 8 0 1 0 Wheat1 0 1 2 3 1 2 2 1 2 3 2 3 0 4 3 4 1 2 0 0 0 Wild oats 1 1 1 2 3 1 3 3 12 5 2 3 0 2 2 6 1 3 0 0 0 Rate 62 g/ha COMPOUND Preemergence 1 2 4 5 6 910 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 B. signalgrass 9 —— 3 1 8 1 2 3 7 0 9 0 3 0 0 0 2 5 9 2 1 0 0 Bedstraw 8 10 — 2 0 4 3 5 21 0 6 0 1 0 0 0 0 6 — 0 1 0 0 Blackgrass 8 3 6 2 0 4 1 3 1 2 0 9 0 2 0 01 1 8 6 0 1 0 0 Cocklebur 2 0 0 0 0 0 — 0 0 0 0 — 0 0 — 0 0 0 1 1 0 0 00 Corn 1 0 0 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 10 9 37 1 9 5 7 4 9 0 9 0 3 0 0 0 3 7 9 1 0 0 1 Giant foxtail 10 10 9 7 2 10 36 5 9 0 10 0 5 0 0 0 5 9 10 0 1 0 2 Morningglory 10 7 1 2 1 8 2 3 4 9 04 0 0 1 0 0 1 3 4 2 3 0 1 Nutsedge 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0— 0 0 0 0 Rape 10 10 2 5 0 9 3 9 0 5 0 6 0 0 0 0 0 2 5 1 0 2 0 1 Redrootpigweed 10 10 3 8 0 9 3 9 7 7 0 6 0 4 0 0 0 7 9 9 0 1 0 2 Soybean 1 0 01 0 1 0 1 0 1 0 0 0 0 0 0 0 0 1 1 0 0 0 0 Sugarbeets 10 10 1 8 0 9 6 106 9 3 10 0 1 3 0 0 7 9 8 2 6 0 0 Velvetleaf 6 6 — 2 1 7 5 3 3 6 0 4 0 00 0 0 4 8 1 0 0 0 0 Wheat 1 1 0 1 0 1 0 0 0 0 0 2 0 0 0 0 0 0 2 2 0 0 00 Wild oats 8 6 2 3 0 5 0 2 1 3 0 8 0 2 2 0 1 4 7 7 0 1 0 0 Rate 62 g/haCOMPOUND Preemergence 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 4445 46 47 49 50 51 52 B. signalgrass 2 1 1 3 2 0 0 0 0 0 0 0 0 2 9 5 6 09 5 0 0 4 8 Bedstraw 2 0 3 — 3 0 0 0 0 0 0 0 — 2 7 8 4 0 8 7 4 2 8 7Blackgrass 2 1 0 1 1 0 0 0 0 0 0 0 0 7 6 2 5 0 8 3 4 3 7 5 Cocklebur 0 00 0 0 0 0 0 0 0 0 0 0 0 1 1 2 0 10 1 0 0 3 1 Corn 0 0 0 0 0 0 0 0 0 0 00 0 0 0 1 0 0 0 1 0 0 4 3 Crabgrass 2 2 1 1 1 0 0 0 0 0 0 0 0 8 9 8 4 09 8 5 6 10 9 Giant foxtail 4 1 1 2 1 0 0 0 0 0 0 0 0 6 10 7 4 0 9 9 5 28 9 Morningglory 2 0 1 0 1 0 0 0 0 0 0 0 0 1 9 9 8 0 10 1 1 1 10 9Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 2 0 — — — — 3 0 Rape 1 1 0 0 20 0 0 0 0 0 0 0 3 7 8 4 0 9 7 7 6 10 9 Redroot pigweed 5 0 2 1 8 0 0 0 00 0 0 0 4 9 10 7 0 10 8 8 7 10 10 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 21 0 0 1 0 0 1 9 4 Sugarbeets 0 0 6 0 8 0 0 0 0 0 0 0 2 3 10 10 9 0 10 76 6 10 10 Velvetleaf 1 0 1 0 6 0 0 0 0 0 0 0 0 1 10 10 8 0 10 8 3 4 1010 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 2 0 0 1 2 1 1 0 2 Wild oats 3 0 10 2 0 0 0 0 0 0 0 0 4 4 6 6 0 6 9 2 3 4 3 Rate 62 g/ha COMPOUNDPreemergence 53 54 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 7677 78 B. signalgrass 0 0 7 2 5 4 4 8 0 9 8 5 8 0 0 1 9 0 8 0 0 0Bedstraw 1 0 3 0 3 0 2 3 0 1 7 3 7 0 — 0 2 0 3 — — 0 Blackgrass 0 0 2 11 1 2 5 0 3 3 3 1 0 1 1 8 0 3 0 0 0 Cocklebur 0 — 0 0 0 0 1 1 0 0 — 0 00 — 0 0 0 0 0 0 0 Corn 0 0 0 0 1 0 0 3 0 0 4 0 0 0 1 3 1 0 0 0 0 0Crabgrass — 0 8 0 3 2 3 9 0 6 6 3 6 0 2 6 10 0 6 0 0 0 Giant foxtail 1 18 2 8 1 2 1 0 0 7 3 4 0 1 5 10 0 1 0 0 0 Morningglory 1 0 6 1 — 1 2 4 02 8 3 8 0 2 2 3 0 6 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 — 0 0 0 — — 0 0 00 0 0 Rape 2 0 5 0 4 0 3 3 0 0 7 2 7 0 2 4 2 0 2 0 0 0 Redroot pigweed 01 8 6 8 8 8 9 0 7 9 8 8 0 6 7 9 0 9 0 0 0 Soybean 0 0 1 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Sugarbeets 4 0 10 6 10 8 10 9 0 9 9 9 9 0 2 8 9 09 0 0 0 Velvetleaf 0 0 7 1 9 1 2 4 0 1 8 2 — 0 — 3 2 0 2 0 0 0 Wheat 0 01 0 1 0 2 0 0 0 3 1 1 0 1 0 2 0 0 0 0 0 Wild oats 0 0 7 0 4 1 3 3 0 2 34 4 0 0 1 7 0 5 0 0 0

Test C

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture which included a surfactant and applied to plants thatwere grown for various periods of time before treatment (postemergenceapplication) using a sandy loam soil mixture.

Plantings of these crops and weed species were adjusted to produceplants of appropriate size for the postemergence test. All plant specieswere grown using normal greenhouse practices. Crop and weed speciesinclude arrowleaf sida (Sida rhombifolia), barnyardgrass (Echinochloacrus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosiaelatior), corn (Zea mays), cotton (Gossypium hirsutum), eastern blacknightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum),field bindweed (Convolvulus arvensis), giant foxtail (Setaria faberii),hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoeahederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed(Polygonum persicaria), lambsquarters (Chenopodium album), largecrabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus),redroot pigweed (Amaranthus retroflexus), soybean (Glycine max), surinamgrass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wildpoinsettia (Euphorbia heterophylla).

Treated plants and untreated controls were maintained in a greenhousefor approximately 14 to 21 days, after which all treated plants werecompared to untreated controls and visually evaluated. Plant responseratings, summarized in Table C, were based upon a 0 to 100 scale where 0was no effect and 100 was complete control. A dash response (−) means notest result.

TABLE C COMPOUND PREEMERGENCE 1 2 3 9 15 21 23 42 43 46 52 66 Rate 140g/ha Arrowleaf sida 100 100 0 95 85 90 100 100 100 100 100 100Barnyardgrass 100 30 0 50 85 5 10 100 50 50 40 5 Cocklebur 0 10 0 0 5 05 60 — 5 20 0 Common ragweed 100 50 0 75 75 20 90 85 50 80 100 30 Corn10 30 0 10 10 0 5 5 55 5 50 0 Cotton 100 15 0 50 10 20 75 60 10 40 70 0E. blacknightsh 95 90 0 95 95 85 100 95 100 100 100 30 Fall panicum 95100 0 100 100 90 100 100 100 100 100 100 Field bindweed 50 100 0 90 10040 100 100 100 100 100 90 Giant foxtail 100 100 0 100 100 100 100 100100 100 100 0 H. beggarticks 100 100 0 85 — 40 100 90 100 100 30 0 I.morningglory 20 5 0 50 65 0 40 100 100 50 100 10 Johnsongrass 100 60 095 100 5 80 85 30 50 80 10 Ladysthumb 95 — — 90 90 5 80 95 — 50 — 70Lambsquarters 100 100 0 100 60 90 100 100 100 100 100 100 Largecrabgrass 100 100 0 100 100 100 100 100 100 100 100 100 Purple nutsedge0 0 0 0 0 0 0 0 0 — 10 0 Redroot pigweed 100 100 0 100 100 100 100 100100 100 100 100 Soybean 0 40 0 25 10 5 10 35 55 20 70 0 Surinam grass 9535 0 90 80 10 60 70 10 25 70 20 Velvetleaf 100 50 0 100 70 50 50 95 10080 100 0 Wild poinsettia 50 45 0 50 20 5 10 85 60 20 100 0 Rate 70 g/haArrowleaf sida 95 20 0 95 85 85 100 95 100 90 100 5 Barnyardgrass 75 5 050 35 0 5 10 30 10 40 5 Cocklebur 0 — 0 0 0 0 — — — 10 0 0 Commonragweed 100 0 0 95 20 0 30 85 40 20 60 0 Corn 10 0 0 5 5 0 0 5 30 0 45 0Cotton 60 5 0 35 10 5 75 60 0 5 0 0 E. blacknightsh 90 5 0 100 95 80 10095 100 100 80 10 Fall panicum 90 5 0 90 80 0 100 85 100 100 100 80 Fieldbindweed 50 30 0 100 100 40 100 100 100 70 100 80 Giant foxtail 100 5 0100 100 100 100 80 100 100 85 0 H. beggarticks 100 40 0 85 — 0 50 — 5100 0 0 I. morningglory 15 5 0 50 20 0 — 70 100 50 100 10 Johnsongrass95 5 0 85 85 0 20 70 30 45 50 5 Ladysthumb 90 30 — 85 20 — 80 85 — 10 —— Lambsquarters 100 — 0 100 20 5 100 100 100 100 100 0 Large crabgrass100 5 0 100 100 100 100 100 100 100 100 100 Purple nutsedge 0 0 0 0 0 00 0 0 — 5 0 Redroot pigweed 100 5 0 100 85 80 100 100 100 100 100 100Soybean 0 0 0 20 10 0 5 5 5 0 55 0 Surinam grass 90 10 0 80 50 5 45 55 55 40 5 Velvetleaf 75 5 0 95 20 50 — 80 100 80 100 0 Wild poinsettia 10 50 50 0 5 5 30 50 15 40 0 Rate 35 g/ha Arrowleaf sida 85 10 0 90 80 70 8095 100 100 100 5 Barnyardgrass 20 0 0 10 10 0 0 5 10 5 30 0 Cocklebur 00 0 0 0 0 — 0 0 0 — 0 Common ragweed 80 0 0 80 10 0 10 20 0 10 40 0 Corn5 0 0 0 0 0 0 5 0 0 0 0 Cotton 30 0 0 10 5 0 5 30 0 0 0 0 E.blacknightsh 90 5 0 95 70 40 95 90 100 80 40 0 Fall panicum 90 0 0 85 4010 55 50 100 60 100 80 Field bindweed 65 0 0 50 65 — 20 95 100 10 100 40Giant foxtail 100 0 0 90 70 85 85 70 100 100 70 0 H. beggarticks 20 40 085 — 0 50 0 0 0 0 0 I. morningglory 15 0 0 20 15 0 5 30 20 45 5 5Johnsongrass 50 5 0 65 35 0 5 70 10 5 40 0 Ladysthumb 25 — — 35 0 0 5 90— 25 — 0 Lambsquarters 100 0 0 95 0 0 60 85 100 60 100 0 Large crabgrass100 0 0 95 100 80 100 80 100 80 100 80 Purple nutsedge 0 0 0 0 0 0 0 0 0— 0 0 Redroot pigweed 100 5 0 100 60 — 100 100 100 70 100 100 Soybean 00 0 20 0 0 5 0 0 0 0 0 Surinam grass 50 0 0 35 20 0 5 50 0 0 5 5Velvetleaf 20 0 0 75 5 0 50 40 100 50 70 0 Wild poinsettia 0 0 0 10 0 05 25 10 0 — 0 COMPOUND Rate 140 g/ha Rate 70 g/ha Rate 35 g/haPOSTEMERGENCE 9 9 9 Arrowleaf sida 90 90 80 Barnyardgrass 25 25 10Cocklebur 80 80 60 Common ragweed 10 30 — Corn 15 15 10 Cotton 90 80 70E. blacknightsh 100 — 100 Fall panicum 30 20 5 Field bindweed 80 70 60Giant foxtail 30 15 15 H. beggarticks 80 70 65 I. morningglory 100 60 50Johnsongrass 50 — 10 Ladysthumb 30 30 20 Lambsquarters 100 80 75 Largecrabgrass 50 40 20 Purple nutsedge 5 5 5 Redroot pigweed — 70 60 Soybean50 50 40 Surinam grass 20 5 5 Velvetleaf 90 70 10 Wild poinsettia 100 9090

Test D

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture which included a surfactant and applied to plants thatwere in the 1- to 4-leaf stage (postemergence application). A mixture ofsandy loam soil and greenhouse potting mix in a 60:40 ratio was used forthe postemergence test.

Plantings of these crops and weed species were adjusted to produceplants of appropriate size for the postemergence test. All plant specieswere grown using normal greenhouse practices. Crop and weed speciesinclude alfalfa (Medicago sativa), annual bluegrass (Poa annua),blackgrass (Alopecurus myosuroides), black nightshade (Solanum nigra),chickweed (Stellaria media), common poppy (Papaver rhoeas), deadnettle(Lamium amplexicaule), downy brome (Bromus tectorum), field violet(Viola arvensis), galium 2 (Galium aparine), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum), jointed goatgrass(Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters(Chenopodium album), lentil (Lens culinaris), littleseed canarygrass(Phalaris minor), pea (Pisum sativum), potato (Solanum tuberosum), rape(Brassica napus), redroot pigweed (Amaranthus retroflexus), Russianthistle (Salsola kali), scentless chamomile (Matricaria inodora),sorghum (Sorghum vulgare), spring barley (Hordeum vulgare), sugar beet(Beta vulgaris), sunflower (Helianthus annuus), ivyleaf speedwell(Veronica hederaefolia), spring wheat (Triticum aestivum), winter wheat(Triticum aestivum), wild buckwheat (Polygonum convolvulus), wildmustard (Sinapis arvensis), wild oat (Avena fatua), windgrass (Aperaspica-venti) and winter barley (Hordeum vulgare).

Treated plants and untreated controls were maintained in a greenhousefor approximately 21 to 28 days, after which all treated plants werecompared to untreated controls and visually evaluated. Plant responseratings, summarized in Table D, are based upon a 0 to 100 scale where 0is no effect and 100 is complete control. A dash response (−) means notest result.

TABLE D COMPOUND Rate 250 g/ha Rate 125 g/ha Rate 62 g/ha Rate 31 g/haPREEMERGENCE 1 22 1 22 52 1 22 46 51 52 1 46 51 52 Alfalfa — — — — — — —— — — — — — — Annual bluegras 85 50 100 100 100 60 20 90 100 100 75 6085 50 Barley (winter) 40 10 30 20 60 20 0 2 90 50 10 50 50 50 Blackgrass70 40 60 60 90 50 30 60 80 80 30 10 60 50 Blk nightshade 100 50 100 6090 90 10 50 95 40 55 50 100 10 Chickweed 90 30 85 70 85 85 40 70 90 8055 70 80 30 Common poppy 100 70 100 70 — 100 60 100 100 — 80 100 100 —Deadnettle 90 10 85 70 90 65 0 90 80 70 60 90 80 50 Downy brome 100 1060 100 50 50 0 70 80 40 30 70 80 30 Field violet 85 — 85 — — 70 — 100 65— 20 85 65 — Galium 100 30 100 100 — 100 20 60 100 — 20 60 100 — Greenfoxtail 100 100 100 100 100 100 10 100 100 80 60 80 100 50 I. Ryegrass100 75 100 65 70 40 0 60 90 70 10 60 60 30 Jointed goatgra 50 10 70 2040 20 0 60 90 40 10 50 60 30 Kochia 85 60 100 65 100 100 10 60 80 80 4060 85 50 Lambsquarters 70 70 70 70 100 70 60 70 70 90 10 65 70 90 Lentil— — — — — — — — — — — — — — LS canarygrass 70 50 85 60 90 60 20 90 90 6020 70 80 30 Pea — — — — — — — — — — — — — — Potato — — — — — — — — — — —— — — Rape 100 50 100 100 100 75 20 100 100 60 30 50 100 50 Redrootpigweed 70 70 75 100 100 70 60 70 70 90 75 70 70 90 Russian thistle 100— — — 85 100 — 30 70 85 10 30 60 30 Scentless chamo 85 70 75 70 — 70 6070 70 — 30 65 65 — Sorghum — — — — — — — — — — — — — — Spring Barley 402 20 10 80 20 0 5 80 60 10 30 70 50 Spring Wheat — 5 0 10 70 0 0 10 7070 0 30 60 60 Sugar beet 100 80 85 100 100 100 30 100 100 100 30 70 100100 Sunflower 30 30 50 10 0 35 20 30 40 0 10 10 40 0 Ivyleaf speedwe 100— 100 — — 100 — 100 100 — 50 100 100 — Wheat (spring) 30 — 50 — — 10 — —— — 10 — — — Wheat (winter) 40 5 20 10 60 10 0 2 55 60 10 40 30 50 Wildbuckwheat 85 30 85 55 100 80 0 40 90 60 40 40 90 40 Wild mustard 98 30100 60 100 100 30 100 100 90 60 90 100 90 Wild oat 90 30 60 30 60 60 070 95 50 20 50 80 40 Windgrass 100 30 100 70 100 100 20 100 100 100 6040 100 80 COMPOUND Rate 125 g/ha Rate 62 g/ha Rate 31 g/ha Rate 16 g/haPOSTEMERGENCE 1 22 52 1 22 52 1 52 1 52 Annual bluegras — 70 50 50 30 2050 20 20 10 Barley (winter) 10 10 10 10 10 10 10 10 5 10 Blackgrass 3020 10 10 10 10 10 10 10 10 Blk nightshade 50 100 65 50 90 65 — 60 60 55Chickweed 70 100 80 80 60 70 — 50 80 30 Common poppy 100 100 100 100 100100 100 100 50 60 Deadnettle 70 90 98 70 50 100 70 100 85 45 Downy brome10 20 20 10 10 20 10 20 2 10 Field violet 80 100 — 100 100 — 100 — 20 —Galium 70 90 60 70 70 65 60 50 0 40 Green foxtail 20 35 30 20 10 10 1010 5 10 I. Ryegrass 10 10 10 10 10 10 10 10 5 5 Jointed goatgra 10 15 1010 10 10 10 10 5 10 Kochia 70 70 70 80 50 70 60 70 0 70 Lambsquarters 5060 80 60 60 80 60 80 0 70 LS canarygrass 20 60 20 20 20 10 10 10 10 10Rape 85 90 85 100 90 98 100 65 65 65 Redroot pigweed 50 70 70 70 50 6070 60 0 45 Russian thistle 50 80 — 60 80 — — — 40 — Scentless chamo 6080 70 60 50 60 60 50 30 30 Spring Barley 10 20 10 10 10 10 10 10 5 10Spring Wheat 20 20 10 10 10 10 10 10 5 10 Sugar beet 100 100 100 90 100100 75 100 45 100 Sunflower 20 20 70 20 10 50 10 20 5 40 Wheat (winter)10 10 10 10 10 10 10 10 5 10 Wild buckwheat 20 20 80 0 20 70 0 50 0 60Wild mustard 100 100 100 100 100 98 100 70 85 60 Wild oat 30 65 10 20 2010 20 10 5 10 Windgrass 30 — 50 — 30 20 20 10 5 10

Test E

Seeds, tubers, or plant parts of alexandergrass (Brachiariaplantaginea), annual bluegrass (Poa annua), arrowleaf sida (Sidarhombifolia), barnyardgrass (Echinochloa crus-galli), bermudagrass(Cynodon dactylon), citrus (Citrus sinensis), common chickweed(Stellaria media), common purslane (Portulaca oleracea), common ragweed(Ambrosia elatior), common groundsel (Senecio vulgaris), dallisgrass(Paspalum dilatatum), goosegrass (Eleusine indica), green foxtail(Setaria viridis), guineagrass (Panicum maximum), itchgrass (Rottboelliaexaltata), johnson grass (Sorghum halepense), kochia (Kochia scoparia),large crabgrass (Digitaria sanguinalis), leafy spurge (Euphorbia esula),pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperusrotundus), quackgrass (Agropyron repens), Russian thistle (Salsolakali), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis),Spanishneedles (Bidens bipinnata), sugarcane (Saccharum officinarum),surinam grass (Brachiaria decumbens) and tall mallow (Malva sylvestris)were planted into greenhouse pots of flats containing greenhouseplanting medium. Plant species were grown grown in separate pots orindividual compartments. Preemergence applications were made within oneday of planting the seed or plant part. Postemergence applications wereapplied when the plants were in the two to four leaf stage (three totwenty cm).

Test chemicals were formulated in a non-phytotoxic solvent mixture whichincluded a surfactant and applied preemergence to the soil surface,postemergence to the plants or as a post directed spray to plants andsoil at the base of the target species. Untreated control plants andtreated plants were placed in the greenhouse and visually evaluated forinjury 13 to 21 days after herbicide application. Plant responseratings, summarized in Table E, are based on a 0 to 100 scale where 0 isno injury and 100 is complete control. A dash (−) response means no testresult.

TABLE E COMPOUND Rate 500 g/ha Rate 250 g/ha PREEMERGENCE 2 1 2 9 15 2342 44 46 67 A. bluegrass — — 100 — 100 — — — — — Alexandergrass 100 100100 100 100 98 90 50 60 95 Arrowleaf sida — — 100 — 100 — — — — — B.signalgrass — — 100 — 98 — — — — — Barnyardgrass — — 100 — 75 — — — — —Bermudagrass 100 100 100 100 98 98 98 100 100 100 Com. purslane 100 100100 100 100 100 100 100 100 100 Com. ragweed 100 100 100 100 100 100 90100 100 100 Com. chickweed — — 100 — 100 — — — — — Com. groundsel 100100 100 100 100 100 100 100 100 100 Dallisgrass 100 100 100 100 100 100100 100 100 100 Goosegrass 100 100 100 100 100 100 100 100 100 100 Greenfoxtail — — 100 — 100 — — — — — Guineagrass — 100 100 100 100 100 100100 98 100 Itchgrass 100 95 95 100 80 70 70 40 40 80 Johnsongrass 100100 100 90 100 90 95 75 0 80 Kochia — — — — 100 — — — — — Largecrabgrass 100 100 100 100 100 100 100 60 100 100 Leafy spurge — — 100 —98 — — — — — P. morninglory 100 100 100 100 90 80 75 50 65 90 Purplenutsedge 0 50 0 0 0 0 30 0 0 10 Quackgrass — — 100 — 95 — — — — —Russian Thistle — — — — 95 — — — — — Sandbur 100 100 100 20 100 98 70 8030 75 Sourgrass 100 100 100 100 100 100 100 100 100 100 Spanishneedles100 100 100 60 100 100 90 98 90 50 Sugarcane — — — — 10 — — — — —Surinam grass 100 100 100 100 100 — 100 — 55 100 Tall Mallow 100 100 100100 98 90 100 98 100 98 COMPOUND Rate 125 g/ha PREEMERGENCE 1 2 9 15 2342 44 46 52 67 A. bluegrass 100 100 — 100 — — — — — — Alexandergrass 90100 65 100 85 90 40 60 75 70 Arrowleaf sida 100 100 — 100 — — — — — — B.signalgrass 100 100 — 95 — — — — — — Barnyardgrass 80 100 — 40 — — — — —— Bermudagrass 100 100 100 98 98 98 98 100 100 90 Com. purslane 100 100100 100 100 100 100 100 100 100 Com. ragweed 100 100 98 98 100 90 98 98100 100 Com. chickweed 100 100 — 98 — — — — — — Com. groundsel 100 100100 100 100 100 100 100 100 95 Dallisgrass 100 100 100 100 90 100 90 10090 80 Goosegrass 100 100 100 98 98 100 98 98 100 100 Green foxtail 100100 — 100 — — — — — — Guineagrass 100 100 90 100 98 100 100 100 100 100Itchgrass 50 75 100 60 70 80 30 40 80 65 Johnsongrass 90 85 85 90 80 9060 0 75 50 Kochia 100 — — 95 — — — — — — Large crabgrass 100 100 100 100100 100 70 100 100 98 Leafy spurge 100 100 — — — — — — — — P.morninglory 100 100 75 75 50 65 50 65 100 90 Purple nutsedge 0 0 0 0 030 0 0 50 5 Quackgrass 100 100 — 95 — — — — — — Russian Thistle — — — 95— — — — — — Sandbur 95 90 10 50 80 70 70 10 50 65 Sourgrass 100 100 100100 100 100 100 100 100 100 Spanishneedles 90 100 30 98 100 100 70 90 3550 Sugarcane — — — 10 — — — — — — Surinam grass 98 100 20 100 — 100 — 4080 75 Tall Mallow 100 100 100 100 85 98 98 100 100 90 COMPOUND Rate 64g/ha PREEMERGENCE 1 2 9 15 23 42 44 46 52 67 A. bluegrass 100 100 — 100— — — — — — Alexandergrass 75 90 65 80 0 40 40 0 75 40 Arrowleaf sida 98100 — 50 — — — — — — B. signalgrass 90 100 — 60 — — — — — —Barnyardgrass 70 95 — 0 — — — — — — Bermudagrass 100 100 98 98 98 95 8098 90 90 Com. purslane 100 100 100 100 100 100 100 100 100 100 Com.ragweed 100 100 100 100 70 75 85 98 80 95 Com. chickweed 95 100 — 85 — —— — — — Com. groundsel 100 100 100 98 100 100 100 100 98 50 Dallisgrass100 100 100 100 85 95 80 98 80 70 Goosegrass 100 100 100 98 98 100 98 90100 90 Green foxtail 100 100 — 100 — — — — — — Guineagrass 100 50 85 10098 95 80 85 80 100 Itchgrass 20 75 85 30 60 65 0 0 70 40 Johnsongrass 4098 75 90 80 90 0 0 50 35 Kochia 100 — — 75 — — — — — — Large crabgrass100 100 100 100 98 90 60 98 100 95 Leafy spurge 95 98 — 65 — — — — — —P. morninglory 80 100 60 40 0 30 30 65 100 75 Purple nutsedge 0 0 0 0 030 0 0 30 5 Quackgrass 80 90 — 65 — — — — — — Russian Thistle — — — 90 —— — — — — Sandbur 65 65 0 20 80 40 60 10 10 60 Sourgrass 100 100 100 10098 100 100 100 100 100 Spanishneedles 80 100 20 30 70 20 60 85 20 0Sugarcane — 0 — 0 — — — — — — Surinam grass 35 90 10 20 — 50 — 0 70 75Tall Mallow 100 100 100 100 85 98 80 100 98 90 COMPOUND Rate 32 g/haPREEMERGENCE 1 2 9 15 23 42 44 46 52 67 A. bluegrass 90 80 — 100 — — — —— — Alexandergrass 10 50 30 75 0 20 0 0 20 25 Arrowleaf sida 98 98 — 65— — — — — — B. signalgrass 20 65 — 35 — — — — — Barnyardgrass 5 20 — 0 —— — — — — Bermudagrass 100 98 70 98 90 90 30 70 70 70 Com. purslane 98100 100 100 100 100 80 100 100 80 Com. ragweed 90 100 10 100 50 50 40 035 90 Com. chickweed 30 100 — 65 — — — — — — Com. groundsel 98 100 98100 100 90 98 100 35 0 Dallisgrass 98 90 85 95 80 70 65 65 35 40Goosegrass 100 95 90 98 98 98 98 85 20 80 Green foxtail 100 90 — 100 — —— — — — Guineagrass 90 50 20 90 80 95 20 60 60 80 Itchgrass 20 70 100 1030 35 0 0 35 40 Johnsongrass 5 65 55 60 70 10 30 0 — 35 Kochia 95 — — 60— — — — — — Large crabgrass 100 98 70 98 98 50 0 90 98 90 Leafy spurge75 60 — 35 — — — — — — P. morninglory 70 100 45 5 0 — 20 65 50 60 Purplenutsedge 0 0 0 0 0 20 0 0 5 0 Quackgrass 65 20 — 65 — — — — — — RussianThistle — — — 70 — — — — — — Sandbur 20 20 0 10 85 0 0 0 0 60 Sourgrass100 100 85 100 98 100 80 98 95 98 Spanishneedles 40 80 0 50 60 20 20 6520 0 Sugarcane — — — 0 — — — — — — Surinam grass 65 50 0 20 — 40 — 0 3035 Tall Mallow 100 98 100 98 80 98 80 100 60 80 COMPOUND Rate Rate Rate500 64 32 g/ha Rate 250 g/ha Rate 125 g/ha g/ha g/ha POSTEMERGENCE 2 1 29 15 23 44 52 2 9 15 44 52 2 2 Alexandergrass 95 90 80 10 20 80 10 75 3010 10 10 10 30 20 Bermudagrass 75 30 50 10 20 10 0 35 35 10 20 0 35 2010 Com. purslane 70 40 70 80 80 50 70 75 65 80 75 70 50 65 65 Com.ragweed 75 70 75 10 10 40 20 80 75 10 5 10 50 — 50 Com. groundsel 75 7540 30 20 40 10 100 20 25 0 10 100 20 0 Dallisgrass 95 90 90 20 50 40 1075 70 10 5 10 5 40 10 Goosegrass 95 70 90 10 30 75 20 75 — 5 20 10 5 7560 Guineagrass 90 70 50 35 40 75 85 85 50 35 20 85 80 — 5 Itchgrass 9585 90 30 85 80 10 40 75 30 80 5 35 40 40 Johnsongrass 95 90 80 85 100 6510 20 60 85 98 5 35 60 10 Large crabgrass 90 85 80 10 40 40 10 80 75 510 10 5 35 35 P. morninglory 90 80 90 50 5 40 40 80 80 40 5 30 80 80 80Purple nutsedge 0 0 0 0 0 0 0 50 0 0 0 0 40 0 0 Sandbur 80 10 50 0 0 200 60 10 0 0 0 5 10 0 Sourgrass 80 30 40 30 25 30 20 50 20 10 20 10 10 2010 Spanishneedles 70 10 — 15 10 10 10 60 40 10 5 10 65 60 60 Sugarcane25 — 25 — — — — — 20 — — — — 20 20 Surinam grass 80 30 70 10 40 — — 7550 10 35 — 75 50 35 Tall Mallow 100 90 100 90 98 90 90 75 100 90 85 8590 95 98

What is claimed is:
 1. A compound selected from Formula I, geometric orstereoisomers thereof, N-oxides thereof and agriculturally suitablesalts thereof,

W is N; X, Y and Z are independently N or CR¹²; R¹ and R² areindependently H, C₁-C₄ alkyl or C₁-C₄alkoxy; R³ is H, F, Cl, Br, cyano,C₁-C₄ alkyl, C₁-C₄ haloalkyl or CO₂R¹⁴; R⁴ is H, F, C₁-C₄ alkyl, OH orOR¹⁴; R³ and R⁴ can be taken together with the carbon to which they areattached to form C(═O) or C(═NOR¹⁴); R⁵ and R⁷ are independently C₁-C₄haloalkyl or C₁-C₄ haloalkoxy; R⁶ is H or F; R⁸ is C₁-C₄ alkyl; R⁹ ishalogen, C₁-C₄ haloalkoxy, C₁-C₄ haloalkyl or S(O)_(n)R¹³; R¹⁰ is H,halogen, cyano or C₁-C₄ haloalkyl; R¹¹ is H, halogen, cyano or C₁-C₄haloalkyl; R¹² is H, halogen, cyano or C₁-C₄ haloalkyl; each R¹³ isindependently C₁-C₄ alkyl or C₁-C₄ haloalkyl; each R¹⁴ is independentlyC₁-C₄ alkyl; and n is
 0. 2. A compound of claim 1 wherein R¹ is C₁-C₄alkyl or C₁-C₄ alkoxy; R² is H; R³ and R⁴ are independently H, F ormethyl; R⁵ and R⁷ are independently C₁-C₂ haloalkyl or C₁-C₂ haloalkoxy;and R⁹ is C₁-C₂ haloalkoxy, C₁-C₂ haloalkyl or S(O)_(n)R¹³.
 3. Acompound of claim 2 wherein J is J-1, J-5 or J-7.
 4. A compound of claim1 wherein R³ and R⁴ can be taken together with the carbon to which theyare attached to form C(═O).
 5. A compound of claim 4 wherein R¹ is C₁-C₄alkyl or C₁-C₄ alkoxy; R² is H; R⁵ and R⁷ are independently C₁-C₂haloalkyl or C₁-C₂ haloalkoxy; and R⁹ is C₁-C₂ haloalkoxy, C₁-C₂haloalkyl or S(O)_(n)R¹³.
 6. A compound of claim 5 wherein J is J-1 orJ-5.
 7. The compound of claim 1 selected from the group consisting of(a)5-ethyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[3-trifluoromethyl)-1H-pyrazol-1-yl]pyrmidine;(b)5-ethyl-4-[[3-(trifluoromethyl)phenyl]methyl]-2-[3(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(c)5-methyl-2-[4-(trifluoromethyl)phenyl]-4-[[3-(trifluoromethyl)phenyl]methyl]pyrimidine;(d)5-methyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[4-trifluoromethyl)phenyl]pyrimidine;(e)5-methyl-4-[[3-(trifluoromethoxy)phenyl]methyl]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(f)[5-methyl-2-[4-(trifluoromethyl)phenyl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone;(g)[5-methyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone;and (h)5-methyl-4-[[3-(trifluoromethyl)phenyl]methyl]-2-[3-(trifluoromethyl-1H-pyrazol-1-yl]pyrimidine.8. A herbicidal composition comprising a herbicidally effective amountof a compound of claim 1 and at least one of a surfactant, a soliddiluent or a liquid diluent.
 9. A method for controlling the growth ofundesired vegetation comprising contacting the vegetation or itsenvironment with a herbicidally effective amount of a compound of claim1.